The Henlopen Conference is a high school sports conference comprising public schools in Kent County and Sussex County in lower Delaware. The teams participate in a variety of sports including football, boys and girls soccer, track and field, cross country, boys and girls basketball, boys and girls indoor track, boys and girls outdoor track, wrestling, boys and girls lacrosse, baseball, softball, cheerleading, boys and girls swimming, and field hockey.
The schools and teams that make up the Henlopen Conference are divided into two divisions, the Henlopen Northern Division and Henlopen Southern Division. Despite the name, the schools are not divided by geographical location, but rather by enrollment numbers, with the larger schools in the Northern Division and the smaller schools in the Southern Division. The conferences are re-arranged every few years based on enrollment numbers.
The current conference alignment for the schools along with the city they are located in are:
Henlopen Northern Division
| School | Team | City | Geographic areas served | |
|---|---|---|---|---|
| Caesar Rodney | Riders | Camden | Camden, Wyoming, Dover Air Force Base, Magnolia, Woodside | |
| Cape Henlopen | Vikings | Lewes | Lewes, Rehoboth Beach, Milton, Harbeson, Cedar Creek, Broadkill Beach | |
| Dover | Senators | Dover | Dover, Cheswold, Hartly, Little Creek, Leipsic | |
| Polytech | Panthers | Woodside | Kent County technical students | |
| Smyrna | Eagles | Smyrna | Smyrna, Clayton, Kenton | |
| Sussex Central | Golden Knights | Georgetown | Georgetown, Millsboro | |
| Sussex Tech | Ravens | Georgetown | Sussex County technical students | |
| Milford | Buccaneers | Milford | Milford, Ellendale, Houston, Lincoln, Thompsonville, Slaughter Beach |
Henlopen Southern Division
| School | Team | City | Geographic areas | |
|---|---|---|---|---|
| Delmar | Wildcats | Delmar | Delmar | |
| Indian River | Indians | Dagsboro | Dagsboro, Frankford, Bethany Beach, Millville, Ocean View, Gumboro, Angola, Oak Orchard, Selbyville, Fenwick Island | |
| Lake Forest | Spartans | Felton | Felton, Bowers Beach, Frederica, Harrington, Viola | |
| Laurel | Bulldogs | Laurel | Laurel, Bethel | |
| Seaford | Blue Jays | Seaford | Seaford, Blades | |
| Sussex Academy of Arts and Sciences | Seahawks | Georgetown | Sussex County - Charter school with lottery-selected admission | |
| Woodbridge | Blue Raiders | Bridgeville | Bridgeville, Greenwood, Farmington |
DateFormat = yyyy
ImageSize = width:1000 height:auto barincrement:20
Period = from:1958 till:2019
TimeAxis = orientation:horizontal
PlotArea = right:20 left:0 bottom:50 top:5 #> to display a count on left side of graph, use "left:20" to suppress the count, use "left:20"<#
Colors = id:barcolor value:rgb(0.99,0.7,0.7)
id:line value:black
id:bg value:white id:Full value:rgb(0.742,0.727,0.852) # Use this color to denote a team that is a member in all sports id:FullxF value:rgb(0.551,0.824,0.777) # Use this color to denote a team that is a member in all sports except for football id:AssocF value:rgb(0.98,0.5,0.445) # Use this color to denote a team that is a member for football only id:AssocOS value:rgb(0.5,0.691,0.824) # Use this color to denote a team that is a member in some sports, but not all (consider identifying in legend or a footnote) id:OtherC1 value:rgb(0.996,0.996,0.699) # Use this color to denote a team that has moved to another conference id:OtherC2 value:rgb(0.988,0.703,0.383) # Use this color to denote a team that has moved to another conference where OtherC1 has already been used, to distinguish the two PlotData=
width:15 textcolor:black shift:(5,-5) anchor:from fontsize:s
bar:1 color:Full from:1959 till:1969 text:Bridgeville Mustangs (1959–1969), then merged with Greenwood to become Woodbridge
bar:2 color:FullxF from:1959 till:1960 text:Delmar Wildcats (1959–Present) bar:2 color:Full from:1960 till:2019
bar:3 color:FullxF from:1959 till:1969 text:Felton Green Devils (1959–1969), then merged with Harrington to become Lake Forest
bar:4 color:FullxF from:1959 till:1967 text:Greenwood Foresters (1959–1968), then merged with Bridgeville to become Woodbridge bar:4 color:Full from:1967 till:1969
bar:5 color:Full from:1959 till:1969 text:Harrington Lions (1959–1969), then merged with Felton to become Lake Forest
bar:6 color:Full from:1959 till:1968 text:John M. Clayton Bears (1959–1968), then merged with Lord Baltimore to become Indian River
bar:7 color:Full from:1959 till:1966 text:Lord Baltimore Lords (1959–1968), then merged with John M. Clayton to become Indian River bar:7 color:FullxF from:1966 till:1968
bar:8 color:Full from:1959 till:1969 text:Millsboro Blue Devils (1959–1969), then merged with Georgetown and became Sussex Central
bar:9 color:FullxF from:1959 till:1964 text:Milton Warriors (1959–1969), then merged with Lewes and Rehoboth Beach to become Cape Henlopen bar:9 color:Full from:1964 till:1969
bar:10 color:Full from:1959 till:1969 text:Rehoboth Beach Seahawks (1959–1969), then merged with Lewes and Milton to become Cape Henlopen
bar:11 color:Full from:1959 till:1969 text:Selbyville Rebels (1959–1969), then merged with Indian River
bar:12 color:Full from:1964 till:1980 text:Dover Air Force Falcons (1964–1980), previously of the Diamond State Conference, closed by Air Force in 1980, students sent to Caesar Rodney
bar:13 color:Full from:1968 till:2019 text:Indian River Indians (1968–Present), consolidation of former members Lord Baltimore and John M. Clayton in 1968, then Selbyville in 1969
bar:14 color:Full from:1969 till:2019 text:Woodbridge Blue Raiders (1969–Present), consolidation of former members Bridgeville and Greenwood
bar:15 color:Full from:1969 till:2019 text:Cape Henlopen Vikings (1969–Present), consolidation of former members Milton and Rehoboth Beach with Lewes of the Diamond State Conference
bar:16 color:Full from:1969 till:2019 text:Caesar Rodney Riders (1969–Present), previously of the Diamond State Conference
bar:17 color:Full from:1969 till:2019 text:Dover Senators (1969–Present), previously of the Diamond State Conference
bar:18 color:Full from:1969 till:2019 text:Lake Forest Spartans (1969–Present), consolidation of former members Harrington and Felton with Frederica
bar:19 color:Full from:1969 till:2019 text:Laurel Bulldogs (1969–Present), previously of the Diamond State Conference
bar:20 color:Full from:1969 till:2019 text:Milford Buccaneers (1969–Present), previously of the Diamond State Conference
bar:21 color:Full from:1969 till:2019 text:Seaford Blue Jays (1969–Present), previously of the Diamond State Conference
bar:22 color:Full from:1969 till:2019 text:Smyrna Eagles (1969–Present), previously of the Diamond State Conference
bar:23 color:Full from:1969 till:2019 text:Sussex Central Golden Knights (1969–Present) consolidation of former member Millsboro with Georgetown of the Diamond State Conference
bar:24 color:AssocOS from:1992 till:1994 text:Polytech Panthers (1992–Present)(All sports except boys basketball until the 1994-95 school year) bar:24 color:Full from:1994 till:2019
bar:25 color:Full from:1995 till:2019 text:Sussex Tech Ravens (1995–Present)
bar:26 color:FullxF from:2015 till:2019 text:Sussex Academy Seahawks (2015–Present)
bar:N color:powderblue from:1959 till:2019 text:Henlopen Conference
ScaleMajor = gridcolor:line unit:year increment:3 start:1959
TextData = fontsize:L textcolor:black pos:(0,30) tabs:(400-center) text:^"Henlopen Conference Membership History"
The Henlopen Conference was created in the January 1959 as a conference of Sussex County schools with enrollments under 350. The conference began its first interleague conference play with the start of the 1959 high school baseball season. The initial members of the Henlopen Conference were the Bridgeville Mustangs, Rehoboth Beach Seahawks, Milton Warriors, Greenwood Foresters, Delmar Wildcats, Millsboro Blue Devils, John M. Clayton Bears, Lord Baltimore Lords, and Selbyville Rebels. While an initial member of the newly formed conference, the Delmar Wildcats did not join the conference for interleague conference play until the beginning of the 1959–60 basketball season. Two weeks later, on February 3, 1959, the Harrington Lions and Felton Green Devils were admitted, expanding the league into Kent County. The Dover Air Force Base Falcons joined two years after its formation.
In 1969, additional teams were added as the Diamond State Conference, originally formed by the larger schools of Kent and Sussex County, merged with the Henlopen Conference. These were: Smyrna, Dover, Caesar Rodney, Milford, Seaford, Lewes, Georgetown and Middletown; Middletown being the lone member from New Castle County. Lewes and Georgetown were the first schools that decided to migrate from the Diamond State Conference and join and eventually every team from the Diamond State Conference (except for Middletown) joined the Henlopen Conference. Middletown, as the only New Castle County school, moved to a conference composed entirely of New Castle County schools after one year of playing as an independent because they were barred from joining the Henlopen Conference due to the conference by-laws regarding geography.
Because of the state mandated school district mergers of 1969–70, the teams changed their geographical makeup. Lewes, Milton, and Rehoboth Beach merged to form the Cape Henlopen Vikings. Georgetown, John M. Clayton, and a large part of the Millsboro School District merged to become the Sussex Central Golden Knights (the other portion of Millsboro was absorbed into Cape Henlopen). Greenwood and Bridgeville merged to become the Woodbridge Blue Raiders. Harrington and Felton merged with Frederica to become the Lake Forest Spartans. Lord Baltimore and Selbyville were merged with Frankford and Dagsboro to become the Indian River Indians. The Milford School District also joined the conference after merging with the Ellendale and Houston school districts, keeping the Milford Buccaneers name. Magnolia and Oak Point merged with Caesar Rodney in 1969 and Dover Air Force Base high school students were absorbed into the Caesar Rodney High School after the United States government closed down the base's school in the 1980s. The Polytech Panthers (1992) and Sussex Tech Ravens (1995) joined the conference with the addition of their sports teams when the schools made the transition from vocational trade schools to technical and academic schools. In August 2015, the Sussex Academy of Arts and Sciences became the newest school, and first charter school, to join the Henlopen Conference.[1]
Of note is that not all teams joined the conference immediately at its inception, affecting the number of conference championships the teams could have won.
Since 1969, teams in the Henlopen Conference have won a total of 25 state football championships. The south leads the north in championships 16 to 9. Caesar Rodney leads the northern division with three Division I Championships and Delmar leads the southern division with six Division II Championships. Woodbridge High School was the last team to win a state championship in 2016.
Only three times has the conference swept the Division I and Division II championship. In 1988, Dover from the North and Indian River from the South were the first to do it. In 2008, Caesar Rodney (North) and Milford (South) accomplished the feat. In the 2008 championship games, both Caesar Rodney and Milford defeated Sussex Central and Laurel to win their respective championships, marking the only time the final four teams in the state tournament were from the Henlopen Conference.[2] In the latest occasion, Woodbridge won the Division II championship and Smyrna won the Division I championship in 2016.
Seaford High School is the only school in the conference to win both a Division I and II Championship.
In 2006 Lake Forest High School had to temporarily shut down their varsity football team due to allegations of use of painkillers. Lake Forest forfeited their final eight games for that season.[3] [4]
Prior to the 2007–08 school year, Milford was moved to the Henlopen South while Smyrna joined the Northern Division due to changes in enrollment. On September 30, 2008, those numbers were rechecked and confirmed to determine the assignments for the 2009–10 and 2010-11 school years. With only a total of 8 students separating the seventh and eighth largest schools, with Polytech coming in a 1,164 and Milford at 1,156; the conference assignments were certified to stay the same through June 2011. This included Polytech in the North Division and Milford in the South.[5]
Days prior to the Division 2 Championship game, Polytech High School challenged the enrollment numbers that were submitted by Milford High School. Polytech brought their case to the athletic directors of the Henlopen Conference schools in a monthly meeting, and Milford argued their case as to why the numbers were correct. At the center of Polytech's argument were 17 students of the Intensive Learning Center, a separate school from Milford High School for special needs and mentally challenged students that rented space inside Milford High. The Polytech officials argued that those students were in the building and should be counted, the Milford officials argued that it was a separate school and that the State of Delaware did not count those children in Milford's enrollment nor did Milford receive funding for them.
A vote was held by the athletic directors of the various schools in the conference, all of the directors in the South voted Milford should move up to the North except Laurel High School; all of the directors in the North said Milford should stay down except for Polytech High School, which made it a 6–6 vote as Milford was not allowed to vote. However, the director for Sussex Central wasn't present for the meeting, so the director for Indian River High School was allowed to vote twice as Indian River High School and Sussex Central High School are in the same school district. The director voted two times that Milford move to the North Division and the vote was confirmed.
In December 2008, Milford appealed to the superintendents of the schools comprising the Henlopen Conference. The superintendents voted to uphold the decision of the athletic directors as it was an athletics issue. Milford also appealed to the Delaware Interscholastic Athletic Association, the governing body for athletics in Delaware schools. The DIAA decided that the matter needed to be handled by the Henlopen Conference and that they would not be involved.
On April 15, 2009, Milford High School filed a lawsuit against the Henlopen Conference in Chancery Court challenging that the vote was against the conference by-laws. In the lawsuit, Milford is listed as seeking "declaratory relief" and to have the vote to change the conference alignments nullified, placing Milford High School back in the South Division.[6] [7] On July 2, that lawsuit was dismissed.[8]
Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Bridgeville | Mustangs | 6 - 0 | 6 - 3 | No playoffs | |
| Rehoboth Beach | Seahawks | 5 - 1 | 5 - 4 | No playoffs | |
| Millsboro | Blue Devils | 4 - 2 | 6 - 2 | No playoffs | |
| Harrington | Lions | 2 - 3 - 1 | 3 - 4 - 1 | No playoffs | |
| Lord Baltimore | Lords | 2 - 4 | 3 - 6 | No playoffs | |
| John M. Clayton | Bears | 1 - 4 - 1 | 2 - 5 - 1 | No playoffs | |
| Selbyville | Rebels | 0 - 6 | 0 - 6 | No playoffs |
Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Millsboro | Blue Devils | 6 - 1 | No playoffs | ||
| Rehoboth Beach | Seahawks | 6 - 1 | No playoffs | ||
| Delmar | Wildcats | 5 - 2 | No playoffs | ||
| Bridgeville | Mustangs | 4 - 3 | No playoffs | ||
| John M. Clayton | Bears | 4 - 3 | No playoffs | ||
| Harrington | Lions | 1 - 6 | No playoffs | ||
| Lord Baltimore | Lords | 1 - 6 | No playoffs | ||
| Selbyville | Rebels | 1 - 6 | No playoffs |
Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Rehoboth Beach | Seahawks | 7 - 0 | No playoffs | ||
| John M. Clayton | Bears | 6 - 1 | No playoffs | ||
| Millsboro | Blue Devils | 5 - 2 | No playoffs | ||
| Bridgeville | Mustangs | 4 - 3 | No playoffs | ||
| Delmar | Wildcats | 3 - 4 | No playoffs | ||
| Harrington | Lions | 1 - 5 - 1 | No playoffs | ||
| Selbyville | Rebels | 1 - 5 - 1 | No playoffs | ||
| Lord Baltimore | Lords | 0 - 7 | No playoffs |
Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Millsboro | Blue Devils | 6 - 0 - 1 | No playoffs | ||
| John M. Clayton | Bears | 5 - 0 - 2 | No playoffs | ||
| Bridgeville | Mustangs | 4 - 3 | No playoffs | ||
| Delmar | Wildcats | 4 - 3 | No playoffs | ||
| Rehoboth Beach | Seahawks | 3 - 3 - 1 | No playoffs | ||
| Lord Baltimore | Lords | 3 - 4 | No playoffs | ||
| Harrington | Lions | 0 - 6 - 1 | No playoffs | ||
| Selbyville | Rebels | 0 - 6 - 1 | No playoffs |
Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| John M. Clayton | Bears | 7 - 0 | 8 - 0 | No playoffs | |
| Millsboro | Blue Devils | 6 - 1 | 7 - 2 | No playoffs | |
| Bridgeville | Mustangs | 3 - 2 - 2 | 5 - 2 - 2 | No playoffs | |
| Rehoboth Beach | Seahawks | 3 - 3 - 1 | 3 - 3 - 1 | No playoffs | |
| Harrington | Lions | 3 - 4 | 3 - 5 | No playoffs | |
| Lord Baltimore | Lords | 2 - 4 - 1 | 3 - 4 - 1 | No playoffs | |
| Delmar | Wildcats | 1 - 6 | 1 - 8 | No playoffs | |
| Selbyville | Rebels | 1 - 6 | 3 - 6 | No playoffs |
Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Harrington | Lions | 8 - 0 - 1 | 8 - 0 - 1 | No playoffs | |
| Bridgeville | Mustangs | 7 - 1 - 1 | 7 - 1 - 1 | No playoffs | |
| Millsboro | Blue Devils | 5 - 2 - 1 | 5 - 2 - 1 | No playoffs | |
| Dover Air Force | Falcons | 5 - 4 | 5 - 4 | No playoffs | |
| John M. Clayton | Bears | 3 - 3 - 3 | 3 - 3 - 3 | No playoffs | |
| Rehoboth Beach | Seahawks | 3 - 3 - 3 | 3 - 3 - 3 | No playoffs | |
| Delmar | Wildcats | 4 - 4 | 4 - 4 | No playoffs | |
| Selbyville | Rebels | 1 - 6 - 1 | 1 - 6 - 1 | No playoffs | |
| Milton | Warriors | 1 - 5 | 1 - 5 | No playoffs | |
| Lord Baltimore | Lords | 0 - 9 | 0 - 9 | No playoffs |
Henlopen Conference
| School | Team | Conference record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Delmar | Wildcats | 8 - 1 | 8 - 1 | No playoffs | |
| John M. Clayton | Bears | 7 - 1 - 1 | 7 - 1 - 1 | No playoffs | |
| Dover Air Force | Falcons | 6 - 3 | 6 - 3 | No playoffs | |
| Lord Baltimore | Lords | 5 - 4 | 5 - 4 | No playoffs | |
| Rehoboth Beach | Seahawks | 5 - 4 | 5 - 4 | No playoffs | |
| Harrington | Lions | 4 - 5 | 4 - 5 | No playoffs | |
| Millsboro | Blue Devils | 4 - 5 | 4 - 5 | No playoffs | |
| Bridgeville | Mustangs | 3 - 5 - 1 | 3 - 5 - 1 | No playoffs | |
| Milton | Warriors | 2 - 7 | 2 - 7 | No playoffs | |
| Selbyville | Rebels | 0 - 9 | 0 - 9 | No playoffs |
Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Sussex Central | Golden Knights | 5 - 0 | 9 - 2 | Loss in semifinals of Div. I playoffs | |
| Caesar Rodney | Riders | 4 - 1 | 6 - 4 | Failed to make playoffs | |
| Dover | Senators | 3 - 2 | 5 - 5 | Failed to make playoffs | |
| Sussex Tech | Ravens | 2 - 3 | 4 - 6 | Failed to make playoffs | |
| Cape Henlopen | Vikings | 1 - 4 | 2 - 8 | Failed to make playoffs | |
| Seaford | Blue Jays | 0 - 5 | 2 - 8 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Delmar | Wildcats | 6 - 0 | 10 - 0 | Won Div. II State Championship | |
| Laurel | Bulldogs | 5 - 1 | 9 - 2 | Loss in semifinals of Div. II playoffs | |
| Smyrna | Eagles | 4 - 2 | 8 - 2 | Failed to make playoffs | |
| Milford | Buccaneers | 2 - 4 | 5 - 5 | Failed to make playoffs | |
| Indian River | Indians | 2 - 4 | 4 - 6 | Failed to make playoffs | |
| Lake Forest | Spartans | 2 - 4 | 4 - 6 | Failed to make playoffs | |
| Woodbridge | Blue Raiders | 0 - 6 | 2 - 8 | Failed to make playoffs |
Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Caesar Rodney | Riders | 5 - 0 | 9 - 2 | Loss in first round of Div. I playoffs | |
| Sussex Central | Golden Knights | 4 - 1 | 8 - 2 | Failed to make playoffs | |
| Dover | Senators | 3 - 2 | 5 - 5 | Failed to make playoffs | |
| Sussex Tech | Ravens | 2 - 3 | 5 - 5 | Failed to make playoffs | |
| Cape Henlopen | Vikings | 1 - 4 | 2 - 8 | Failed to make playoffs | |
| Seaford | Blue Jays | 0 - 5 | 3 - 7 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Smyrna | Eagles | 5 - 1 | 9 - 2 | Loss in semifinals of Div. II playoffs | |
| Indian River | Indians | 5 - 1 | 7 - 4 | Loss in semifinals of Div. II playoffs | |
| Lake Forest | Spartans | 4 - 2 | 6 - 4 | Failed to make playoffs | |
| Milford | Buccaneers | 3 - 3 | 5 - 5 | Failed to make playoffs | |
| Laurel | Bulldogs | 3 - 3 | 4 - 6 | Failed to make playoffs | |
| Woodbridge | Blue Raiders | 1 - 5 | 2 - 7 | Failed to make playoffs | |
| Delmar | Wildcats | 0 - 6 | 1 - 9 | Failed to make playoffs |
Henlopen Northern Division[9]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Caesar Rodney | Riders | 5 – 0 | 9 – 2 | Loss in semifinals of Div. I playoffs | |
| Sussex Tech | Ravens | 4 – 1 | 7 – 4 | Loss in first round of Div. I playoffs | |
| Milford | Buccaneers | 3 – 2 | 7 – 3 | Failed to make playoffs | |
| Sussex Central | Golden Knights | 2 – 3 | 5 – 5 | Failed to make playoffs | |
| Dover | Senators | 1 – 4 | 3 – 7 | Failed to make playoffs | |
| Cape Henlopen | Vikings | 0 – 5 | 0 – 10 | Failed to make playoffs |
Henlopen Southern Division[10]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Indian River | Indians | 5 – 1 | 8 – 4 | Loss in semifinals of Div. II playoffs | |
| Woodbridge | Blue Raiders | 4 – 2 | 7 – 3 | Failed to make playoffs | |
| Smyrna | Eagles | 4 – 2 | 7 – 4 | Loss in first round of Div. II playoffs | |
| Laurel | Bulldogs | 4 – 2 | 7 – 4 | Loss in first round of Div. II playoffs | |
| Delmar | Wildcats | 2 – 4 | 3 – 7 | Failed to make playoffs | |
| Seaford | Blue Jays | 1 – 5 | 3 – 7 | Failed to make playoffs | |
| Lake Forest | Spartans | 1 – 5 | 3 – 7 | Failed to make playoffs |
Delaware high school playoffs were expanded from a four team field in both Division I and Division II to six team field for both divisions beginning with the 2004 season.
Henlopen Northern Division[11]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Dover | Senators | 5 – 0 | 8 – 3 | Loss in first round of Div. I playoffs | |
| Caesar Rodney | Riders | 3 – 2 | 4 – 6 | Failed to make playoffs | |
| Sussex Central | Golden Knights | 2 – 3 | 6 – 5 | Loss in first round of Div. I playoffs | |
| Sussex Tech | Ravens | 2 – 3 | 5 – 5 | Failed to make playoffs | |
| Cape Henlopen | Vikings | 2 – 3 | 4 – 6 | Failed to make playoffs | |
| Milford | Buccaneers | 1 – 4 | 4 – 6 | Failed to make playoffs |
Henlopen Southern Division[12]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Indian River | Indians | 6 – 0 | 9 – 2 | Loss in semifinals of Div. II playoffs | |
| Laurel | Bulldogs | 5 – 1 | 8 – 3 | Loss in first round of Div. II playoffs | |
| Delmar | Wildcats | 4 – 2 | 8 – 2 | Failed to make playoffs | |
| Lake Forest | Spartans | 3 – 3 | 4 – 6 | Failed to make playoffs | |
| Smyrna | Eagles | 2 – 4 | 5 – 5 | Failed to make playoffs | |
| Woodbridge | Blue Raiders | 1 – 5 | 3 – 7 | Failed to make playoffs | |
| Seaford | Blue Jays | 0 – 6 | 0 – 10 | Failed to make playoffs |
Henlopen Northern Division[13]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Sussex Central | Golden Knights | 5 – 0 | 11 – 1 | Loss in Div. I Championship Game | |
| Milford | Buccaneers | 3 – 2 | 6 – 4 | Failed to make playoffs | |
| Cape Henlopen | Vikings | 3 – 2 | 5 – 5 | Failed to make playoffs | |
| Caesar Rodney | Riders | 2 – 3 | 5 – 5 | Failed to make playoffs | |
| Dover | Senators | 3 – 3 | 5 – 5 | Failed to make playoffs | |
| Sussex Tech | Ravens | 0 – 5 | 2 – 8 | Failed to make playoffs |
Henlopen Southern Division[4]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Delmar | Wildcats | 6 – 0 | 11 – 1 | Loss in Div. II Championship Game | |
| Indian River | Indians | 5 – 1 | 8 – 3 | Loss in first round of Div. II playoffs | |
| Woodbridge | Blue Raiders | 4 – 2 | 6 – 4 | Failed to make playoffs | |
| Laurel | Bulldogs | 3 – 3 | 6 – 4 | Failed to make playoffs | |
| Smyrna | Eagles | 2 – 4 | 3 – 7 | Failed to make playoffs | |
| Seaford | Blue Jays | 1 – 5 | 2 – 8 | Failed to make playoffs | |
| Lake Forest | Spartans | 1 – 5 | 1 – 9 | Failed to make playoffs |
Henlopen Northern Division[14]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Sussex Central | Golden Knights | 6 – 0 | 10 – 2 | Loss in Div. I Championship Game | |
| Caesar Rodney | Riders | 4 – 2 | 6 – 5 | Loss in first round of Div. I playoffs | |
| Sussex Tech | Ravens | 4 – 2 | 7 – 3 | Failed to make playoffs | |
| Dover | Senators | 3 – 3 | 5 – 5 | Failed to make playoffs | |
| Cape Henlopen | Vikings | 3 – 3 | 4 – 6 | Failed to make playoffs | |
| Smyrna | Eagles | 1 – 5 | 3 – 7 | Failed to make playoffs | |
| Polytech | Panthers | 0 – 6 | 2 – 8 | Failed to make playoffs |
Henlopen Southern Division[15]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Delmar | Wildcats | 6 – 0 | 10 – 1 | Loss in semifinals of Div. II playoffs | |
| Indian River | Indians | 5 – 1 | 8 – 3 | Loss in first round of Div. II playoffs | |
| Milford | Buccaneers | 4 – 2 | 6 – 4 | Failed to make playoffs | |
| Woodbridge | Blue Raiders | 3 – 3 | 4 – 6 | Failed to make playoffs | |
| Laurel | Bulldogs | 2 – 4 | 5 – 5 | Failed to make playoffs | |
| Lake Forest | Spartans | 1 – 5 | 1 – 9 | Failed to make playoffs | |
| Seaford | Blue Jays | 0 – 6 | 1 – 9 | Failed to make playoffs |
Henlopen Northern Division[16]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Sussex Central | Golden Knights | 6 – 0 | 10 – 2 | Loss in Div. I Championship Game | |
| Caesar Rodney | Riders | 5 – 1 | 11 – 1 | Won Div. I State Championship | |
| Dover | Senators | 4 – 2 | 6 – 4 | Failed to make playoffs | |
| Smyrna | Eagles | 2 – 4 | 5 – 5 | Failed to make playoffs | |
| Sussex Tech | Ravens | 2 – 4 | 4 – 6 | Failed to make playoffs | |
| Cape Henlopen | Vikings | 2 – 4 | 3 – 7 | Failed to make playoffs | |
| Polytech | Panthers | 0 – 6 | 2 – 8 | Failed to make playoffs |
Henlopen Southern Division[17]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Milford | Buccaneers | 5 – 1 | 10 – 2 | Won Div. II State Championship | |
| Laurel | Bulldogs | 5 – 1 | 9 – 3 | Loss in Div. II State Championship Game | |
| Indian River | Indians | 4 – 2 | 7 – 4 | Loss in first round of Div. II playoffs | |
| Delmar | Wildcats | 4 – 2 | 8 – 2 | Failed to make playoffs | |
| Seaford | Blue Jays | 2 – 4 | 2 – 8 | Failed to make playoffs | |
| Lake Forest | Spartans | 1 – 5 | 3 – 7 | Failed to make playoffs | |
| Woodbridge | Blue Raiders | 0 – 6 | 0 – 10 | Failed to make playoffs |
The week one meeting between Milford and St. Marks (Wilmington, Delaware) was ranked the #10 matchup in the nation by MaxPreps.[18]
Henlopen Northern Division[19]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Sussex Tech | Ravens | 5 – 1 | 9 – 2 | Loss in first round of Div. I playoffs | |
| Caesar Rodney | Riders | 5 – 1 | 8 – 4 | Loss in semifinals of Div. I playoffs | |
| Milford | Buccaneers | 5 – 1 | 6 – 4 | Failed to make playoffs | |
| Sussex Central | Golden Knights | 2 – 4 | 6 – 4 | Failed to make playoffs | |
| Dover | Senators | 2 – 4 | 4 – 6 | Failed to make playoffs | |
| Smyrna | Eagles | 2 – 4 | 2 – 8 | Failed to make playoffs | |
| Cape Henlopen | Vikings | 0 – 6 | 1 – 9 | Failed to make playoffs |
Henlopen Southern Division[20]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Delmar | Wildcats | 6 – 0 | 10 – 3 | Won Div. II State Championship | |
| Laurel | Bulldogs | 5 – 1 | 8 – 3 | Loss in semifinals of Div. II playoffs | |
| Lake Forest | Spartans | 4 – 2 | 7 – 3 | Failed to make playoffs | |
| Indian River | Indians | 3 – 3 | 5 – 5 | Failed to make playoffs | |
| Seaford | Blue Jays | 2 – 4 | 4 – 6 | Failed to make playoffs | |
| Polytech | Panthers | 1 – 5 | 1 – 9 | Failed to make playoffs | |
| Woodbridge | Blue Raiders | 0 – 6 | 3 – 7 | Failed to make playoffs |
Henlopen Northern Division[21]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Sussex Central | Golden Knights | 5 – 1 | 7 – 4 | Loss in first round of Div. I playoffs | |
| Caesar Rodney | Riders | 5 – 1 | 7 – 4 | Loss in first round of Div. I playoffs | |
| Dover | Senators | 3 – 3 | 6 – 4 | Failed to make playoffs | |
| Sussex Tech | Ravens | 3 – 3 | 5 – 5 | Failed to make playoffs | |
| Cape Henlopen | Vikings | 2 – 4 | 5 – 5 | Failed to make playoffs | |
| Smyrna | Eagles | 2 – 4 | 4 – 6 | Failed to make playoffs | |
| Milford | Buccaneers | 1 – 5 | 3 – 7 | Failed to make playoffs |
Henlopen Southern Division[22]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Lake Forest | Spartans | 5 – 1 | 8 – 3 | Loss in first round of Div. II playoffs | |
| Delmar | Wildcats | 4 – 2 | 8 – 4 | Loss in semifinals of Div. II playoffs | |
| Laurel | Bulldogs | 4 – 2 | 5 – 5 | Failed to make playoffs | |
| Indian River | Indians | 4 – 2 | 5 – 5 | Failed to make playoffs | |
| Polytech | Panthers | 3 – 3 | 4 – 6 | Failed to make playoffs | |
| Woodbridge | Blue Raiders | 1 – 5 | 3 – 7 | Failed to make playoffs | |
| Seaford | Blue Jays | 0 – 6 | 2 – 8 | Failed to make playoffs |
Henlopen Northern Division[23]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Sussex Central | Golden Knights | 6 – 0 | 7 – 4 | Loss in first round of Div. I playoffs | |
| Dover | Senators | 5 – 1 | 8 – 4 | Loss in semifinals of Div. I playoffs | |
| Cape Henlopen | Vikings | 4 – 2 | 8 – 2 | Failed to make playoffs | |
| Caesar Rodney | Riders | 3 – 3 | 3 – 7 | Failed to make playoffs | |
| Smyrna | Eagles | 2 – 4 | 5 – 5 | Failed to make playoffs | |
| Sussex Tech | Ravens | 1 – 5 | 4 – 6 | Failed to make playoffs | |
| Milford | Buccaneers | 0 – 6 | 1 – 9 | Failed to make playoffs |
Henlopen Southern Division[24]
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Indian River | Indians | 6 – 0 | 12 – 0 | Won Div. II State Championship | |
| Delmar | Wildcats | 5 – 1 | 9 – 2 | Loss in first round of Div. II playoffs | |
| Laurel | Bulldogs | 4 – 2 | 4 – 6 | Failed to make playoffs | |
| Lake Forest | Spartans | 3 – 3 | 5 – 5 | Failed to make playoffs | |
| Polytech | Panthers | 2 – 4 | 2 – 8 | Failed to make playoffs | |
| Woodbridge | Blue Raiders | 1 – 5 | 2 – 8 | Failed to make playoffs | |
| Seaford | Blue Jays | 0 – 6 | 0 – 10 | Failed to make playoffs |
Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Sussex Central | Golden Knights | 5 – 1 | 8 – 3 | Loss in first round of Div. I playoffs | |
| Cape Henlopen | Vikings | 5 – 1 | 8 – 3 | Loss in first round of Div. I playoffs | |
| Caesar Rodney | Riders | 5 – 1 | 8 – 4 | Loss in semi-finals of Div. I playoffs | |
| Dover | Senators | 3 – 3 | 5 – 5 | Failed to make playoffs | |
| Sussex Tech | Ravens | 2 – 4 | 3 – 7 | Failed to make playoffs | |
| Smyrna | Eagles | 1 – 5 | 4 – 6 | Failed to make playoffs | |
| Milford | Buccaneers | 0 – 6 | 3 – 7 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Indian River | Indians | 6 – 0 | 9 – 3 | Loss in semi-finals of Div. II playoffs | |
| Delmar | Wildcats | 5 – 1 | 7 – 3 | Failed to make playoffs | |
| Lake Forest | Spartans | 4 – 2 | 5 – 5 | Failed to make playoffs | |
| Laurel | Bulldogs | 3 – 3 | 4 – 6 | Failed to make playoffs | |
| Woodbridge | Blue Raiders | 2 – 4 | 2 – 8 | Failed to make playoffs | |
| Seaford | Blue Jays | 1 – 5 | 1 – 9 | Failed to make playoffs | |
| Polytech | Panthers | 0 – 6 | 1 – 9 | Failed to make playoffs |
Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Caesar Rodney | Riders | 6 – 0 | 8 – 4 | Loss in semi-finals of Div. I playoffs | |
| Dover | Senators | 5 – 1 | 9 – 3 | Loss in semi-finals of Div. I playoffs | |
| Cape Henlopen | Vikings | 4 – 2 | 6 – 4 | Failed to make playoffs | |
| Sussex Tech | Ravens | 3 – 3 | 5 – 5 | Failed to make playoffs | |
| Sussex Central | Golden Knights | 2 – 4 | 5 – 5 | Failed to make playoffs | |
| Polytech | Panthers | 1 – 5 | 5 – 5 | Failed to make playoffs | |
| Smyrna | Eagles | 0 – 6 | 2 – 8 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Indian River | Indians | 5 – 1 | 6 – 5 | Loss in first round of Div. II playoffs | |
| Delmar | Wildcats | 5 – 1 | 9 – 2 | Loss in first round of Div. II playoffs | |
| Woodbridge | Blue Raiders | 4 – 2 | 8 – 4 | Loss in semi-finals of Div. II playoffs | |
| Lake Forest | Spartans | 4 – 2 | 6 – 4 | Failed to make playoffs | |
| Laurel | Bulldogs | 2 – 4 | 2 – 8 | Failed to make playoffs | |
| Milford | Buccaneers | 1 – 5 | 1 – 9 | Failed to make playoffs | |
| Seaford | Blue Jays | 0 – 6 | 3 – 7 | Failed to make playoffs |
Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Sussex Tech | Ravens | 6 – 0 | 10 – 2 | Loss in semifinals of Div. I playoffs | |
| Cape Henlopen | Vikings | 4 – 2 | 8 – 2 | Failed to make playoffs | |
| Smyrna | Eagles | 3 – 3 | 5 – 5 | Failed to make playoffs | |
| Sussex Central | Golden Knights | 3 – 3 | 5 – 5 | Failed to make playoffs | |
| Caesar Rodney | Riders | 2 – 4 | 2 – 8 | Failed to make playoffs | |
| Dover | Senators | 2 - 4 | 3 - 7 | Failed to make playoffs | |
| Polytech | Panthers | 1 – 5 | 4 – 6 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Lake Forest | Spartans | 6 – 0 | 10 – 1 | Loss in first round of Div. II playoffs | |
| Laurel | Bulldogs | 5 – 1 | 10 – 3 | Loss in Div. II Championship Game | |
| Delmar | Wildcats | 4 – 2 | 5 – 5 | Failed to make playoffs | |
| Indian River | Indians | 3 - 3 | 4 - 6 | Failed to make playoffs | |
| Woodbridge | Blue Raiders | 2 – 4 | 4 – 6 | Failed to make playoffs | |
| Milford | Buccaneers | 1 – 5 | 1 – 9 | Failed to make playoffs | |
| Seaford | Blue Jays | 0 – 6 | 1 – 9 | Failed to make playoffs |
Henlopen Northern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Smyrna | Eagles | 6 – 0 | 12 – | Won Div. I State Championship | |
| Sussex Tech | Ravens | 5 – 1 | 8 – 3 | Loss in first round of Div. I playoffs | |
| Sussex Central | Golden Knights | 4 – 2 | 6 – 4 | Failed to make playoffs | |
| Cape Henlopen | Vikings | 3 – 3 | 5 – 4 | Failed to make playoffs | |
| Dover | Senators | 2 – 4 | 4 – 6 | Failed to make playoffs | |
| Caesar Rodney | Riders | 1 - 5 | 2 - 8 | Failed to make playoffs | |
| Polytech | Panthers | 0 – 6 | 0 – 10 | Failed to make playoffs |
Henlopen Southern Division
| School | Team | Division Record | Overall record | Season Outcome | |
|---|---|---|---|---|---|
| Lake Forest | Spartans | 6 – 0 | 8 – 3 | Loss in first round of Div. II playoffs | |
| Woodbridge | Blue Raiders | 5 – 1 | 8 – 4 | Loss in semifinals of Div. II playoffs | |
| Indian River | Indians | 4 – 2 | 4 – 6 | Failed to make playoffs | |
| Milford | Buccaneers | 3 - 3 | 6 - 4 | Failed to make playoffs | |
| Laurel | Bulldogs | 2 – 4 | 3 – 7 | Failed to make playoffs | |
| Delmar | Wildcats | 1 – 5 | 1 – 9 | Failed to make playoffs | |
| Seaford | Blue Jays | 0 – 6 | 0 – 10 | Failed to make playoffs |
Of note: Teams with a gold background went on to win the State Championship.
| Year | Henlopen South (Div II) | Henlopen North (Div I) | |
|---|---|---|---|
| 2020 | Woodbridge | Smyrna | |
| 2019 | Delmar | Smyrna | |
| 2018 | Woodbridge | Sussex Central | |
| 2017 | Delmar | Smyrna | |
| 2016 | Woodbridge | Smyrna | |
| 2015 | Lake Forest | Smyrna | |
| 2014 | Lake Forest | Sussex Tech | |
| 2013 | Indian River | Caesar Rodney | |
| 2012 | Indian River | Sussex Central | |
| 2011 | Indian River | Sussex Central | |
| 2010 | Lake Forest | Sussex Central | |
| 2009 | Delmar | Sussex Tech | |
| 2008 | Milford | Sussex Central | |
| 2007 | Delmar | Sussex Central | |
| 2006 | Delmar | Sussex Central | |
| 2005 | Indian River | Dover | |
| 2004 | Indian River | Caesar Rodney | |
| 2003 | Indian River | Caesar Rodney | |
| 2002 | Delmar | Sussex Central | |
| 2001 | Delmar | Dover | |
| 2000 | Delmar | Caesar Rodney | |
| 1999 | Woodbridge | Caesar Rodney | |
| 1998 | Delmar | Cape Henlopen | |
| 1997 | Delmar | Cape Henlopen | |
| 1996 | Delmar | Caesar Rodney | |
| 1995 | Delmar | Caesar Rodney | |
| 1994 | Seaford | Caesar Rodney | |
| 1993 | Laurel | Seaford | |
| 1992 | Laurel | Seaford | |
| 1991 | Lake Forest | Caesar Rodney | |
| 1990 | Lake Forest | Caesar Rodney | |
| 1989 | Lake Forest | Caesar Rodney | |
| 1988 | Indian River | Dover | |
| 1987 | Indian River | Seaford | |
| 1986 | Laurel, Indian River, Smyrna | Seaford, Caesar Rodney, Dover | |
| 1985 | Delmar | Seaford | |
| 1984 | Lake Forest | Cape Henlopen | |
| 1983 | Seaford | Caesar Rodney | |
| 1982 | Seaford | Dover, Cape Henlopen | |
| 1981 | Lake Forest | Seaford | |
| 1980 | Indian River | Caesar Rodney | |
| 1979 | Indian River | Cape Henlopen | |
| 1978 | Dover Air Force Base*** | Caesar Rodney | |
| 1977 | Smyrna | Caesar Rodney | |
| 1976 | Delmar | Caesar Rodney | |
| 1975 | Smyrna | Caesar Rodney | |
| 1974 | Smyrna | Milford | |
| 1973 | Smyrna | Caesar Rodney, Sussex Central | |
| 1972 | Lake Forest | Dover | |
| 1971 | Laurel | Dover | |
| 1970 | Indian River | Sussex Central | |
| 1969 | Indian River | Smyrna |
Prior to 1969 there were no North and South divisions, simply an overall champion. They were:
| Year | Henlopen Conference Champion | |
|---|---|---|
| 1968 | Indian River | |
| 1967 | Bridgeville (Woodbridge) | |
| 1966 | Bridgeville (Woodbridge) | |
| 1965 | Delmar | |
| 1964 | Harrington (Lake Forest) | |
| 1963 | John M. Clayton (Indian River) | |
| 1962 | Millsboro / John M. Clayton (Sussex Central / Indian River) | |
| 1961 | Rehoboth (Cape Henlopen) | |
| 1960 | Millsboro / Rehoboth (Sussex Central / Cape Henlopen) | |
| 1959 | Bridgeville (Woodbridge) |
Note that of those pre-1969 teams listed above, only Indian River and Delmar still exist as school districts today, with Indian River's merger coming prior to the 1969–70 school year.
| School | Division | Total | Notes | |
|---|---|---|---|---|
| Caesar Rodney | North | 19 | Most all time in Northern Division | |
| Cape Henlopen | North | 7 | Includes two wins by Rehoboth | |
| Delmar | South | 14 | ||
| Dover | North | 6 | ||
| Dover AF | n/a | 1 | defunct | |
| Indian River | South | 16 | Includes two won by John M Clayton – Most all time in the Southern Division | |
| Lake Forest | South | 10 | Includes one won by Harrington | |
| Laurel | South | 4 | ||
| Milford | North | 2 | One in the North; One in the South | |
| Polytech | South | 0 | ||
| Seaford | South | 9 | Six in the North; Three in the South | |
| Smyrna | North | 9 | Four in the North; Five in the South | |
| Sussex Central | North | 11 | Includes two won by Millsboro | |
| Sussex Tech | North | 2 | ||
| Woodbridge | South | 6 | Includes three won by Bridgeville |
Battle of the Bell Milford vs. Lake Forest – Started in 1969 when the conferences were formed and school districts were consolidated. The winning team keeps the trophy, the bell off a train that used to run between Milford and Harrington, for a year until the next Battle of the Bell.
2013 Battle of the Bell Champion – Lake Forest (33-7)
Delaware's Oldest High School Rivalry Seaford vs. Laurel – The oldest rivalry game in the state, and said to be the third oldest rivalry in the nation, these two towns are separated by only 6 miles and a large turn-out is always expected.
2013 Delaware's Oldest High School Rivalry Champion – Laurel (46-6)
The Civil War Caesar Rodney vs. Dover – A cross-town rivalry game in Dover.
2013 Civil War Champion – Caesar Rodney (42-18)
The Battle for Georgetown Sussex Tech vs. Sussex Central – A cross-town rivalry game in Georgetown.
2013 Battle for Georgetown Champion – Sussex Tech (28-27)
The Tech Bowl Sussex Tech vs. Polytech – A rivalry game between Sussex County and Kent County's two technical high schools.
2013 Tech Bowl Champion – Sussex Tech (35-28)
The Harvest Bowl Smyrna vs. Middletown – A non-conference rivalry game going back to before the Henlopen Conference when the two teams played in the Diamond State Conference.
2012 Harvest Bowl Champion – Middletown (47-19)
Battle for the Lions Club Trophy Delmar vs. Laurel – The two towns are only 9 miles apart along U.S. 13 and the winner takes home a trophy sponsored by the local Lions Club.
2013 Battle for the Lions Club Trophy Champion – Delmar (21-20)
Intra-district Rivalry Sussex Central vs. Indian River – A rivalry game between the two schools that belong to the Indian River School District. The IRSD is one of the largest districts in the state of Delaware.
2013 Intra-district Rivalry Champion – Sussex Central (29-27)
| Year | Henlopen South | Henlopen North | Conference Dual Meet | Tournament champion | |
|---|---|---|---|---|---|
| 2011-12 | Polytech | Caesar Rodney | No longer awarded | Caesar Rodney | |
| 2010-11 | Seaford, Polytech, Indian River | Sussex Central | No longer awarded | Caesar Rodney | |
| 2009-10 | Sussex Central | No longer awarded | Sussex Central | ||
| 2008-09 | Milford | Caesar Rodney | Caesar Rodney | Smyrna | |
| 2007-08 | Indian River | Sussex Central | Sussex Central | Sussex Central | |
| 2006-07 | Caesar Rodney | Caesar Rodney | Caesar Rodney | ||
| 2005-06 | Caesar Rodney | Caesar Rodney | Caesar Rodney | ||
| 2004-05 | Milford | Sussex Central | Sussex Central | ||
| 2003-04 | Laurel | Caesar Rodney | Sussex Central | Sussex Central | |
| 2002-03 | Smyrna | Caesar Rodney | Caesar Rodney | Sussex Central | |
| 2001-02 | Lake Forest | Caesar Rodney | Caesar Rodney | Sussex Central | |
| 2000-01 | Milford | Caesar Rodney | Caesar Rodney | Caesar Rodney | |
| 1999-00 | Milford | Caesar Rodney | Caesar Rodney | Caesar Rodney | |
| 1998 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney | |
| 1997 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney | |
| 1996 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney | |
| 1995 | Smyrna | Sussex Central | Smyrna | Smyrna | |
| 1994 | Smyrna | Dover | Dover | Dover | |
| 1993 | Smyrna | Dover | Dover | Dover | |
| 1992 | Smyrna | Dover | Dover | Dover | |
| 1991 | Smyrna | Dover | Smyrna | Dover | |
| 1990 | Smyrna | Cape Henlopen | Smyrna | Smyrna | |
| 1989 | Smyrna | Sussex Central | Smyrna | Smyrna | |
| 1988 | Smyrna | Dover | Dover | Dover | |
| 1987 | Smyrna | Dover | Smyrna | Dover | |
| 1986 | Smyrna | Dover | Smyrna | Dover | |
| 1985 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney | |
| 1984 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney | |
| 1983 | Laurel | Caesar Rodney | Caesar Rodney | Caesar Rodney | |
| 1982 | Smyrna | Caesar Rodney | Caesar Rodney | Caesar Rodney | |
| 1981 | Smyrna | Milford | Milford | None | |
| 1980 | Smyrna | Milford | Milford | None | |
| 1979 | Smyrna | Caesar Rodney | Smyrna | None | |
| 1978 | Smyrna | Caesar Rodney | Smyrna | None | |
| 1977 | Smyrna | Caesar Rodney | Caesar Rodney | None | |
| 1976 | Smyrna | Sussex Central | Sussex Central | None | |
| 1975 | Smyrna | Sussex Central | Smyrna | None | |
| 1974 | Smyrna | Caesar Rodney | Caesar Rodney | None | |
| 1973 | Smyrna | Caesar Rodney | Caesar Rodney | None | |
| 1972 | Smyrna | Caesar Rodney | Smyrna, Caesar Rodney, Sussex Central | None | |
| 1971 | Smyrna | Sussex Central | Smyrna | None | |
| 1970 | Smyrna | Sussex Central | Smyrna | None | |
| 1969 | None | None | None | Harrington | |
| 1968 | None | None | None | ? | |
| 1967 | None | None | None | Delmar | |
| 1966 | None | None | None | Harrington | |
| 1965 | None | None | None | Delmar | |
| 1964 | None | None | None | Millsboro |
Prior to 1969 there were no conferences, simply a Tournament champion. In 1970 the school districts consolidated. Of those pre-1969 teams, only Indian River and Delmar still exist as school districts today, with Indian River's merger coming prior to 1969–70.
Total Division Championships:
Caesar Rodney – 21 (most all time in the North)
Cape Henlopen – 1
Delmar – 0
Dover – 7
Indian River – 2
Lake Forest – 0
Laurel – 2
Milford – 6 *Only team to win championships in both the North & South (2 in North, 4 in South)
Polytech – 0
Seaford – 0
Smyrna – 29 (Most by any school, in any conference, in any sport in the state)
Sussex Central – 7
Sussex Tech – 0
Woodbridge – 0
Conference Dual Meet Championships (Overall Champion):
Caesar Rodney – 16 (most all time)
Cape Henlopen – 0
Delmar – 0
Dover – 4
Indian River – 0
Lake Forest – 0
Laurel – 0
Milford – 2 *One of only 2 Sussex County schools to win overall championship
Polytech – 0
Seaford – 0
Smyrna – 12
Sussex Central – 5 *One of only 2 Sussex County schools to win overall championship
Sussex Tech – 0
Woodbridge – 0
Tournament championships:
Caesar Rodney – 10 (most all time)
Cape Henlopen – 0
Delmar – 2
Dover – 7
Indian River – 0
Lake Forest – 2 *Both won by Harrington prior to 1970 merger
Laurel – 0
Milford – 0
Polytech – 0
Seaford – 0
Smyrna – 4
Sussex Central – 4
Sussex Tech – 0
Woodbridge – 0
| Year | Henlopen South Division | Henlopen North Division | Conference Championship Game | Conference Champion | |
|---|---|---|---|---|---|
| 2016-17 | Woodbridge | Smyrna[25] | Smyrna 61 - Woodbridge 51 | Smyrna | |
| 2015-16 | |||||
| 2014-15 | |||||
| 2013-14 Woodbridge Boys Henlopen Conference Championship Beat Caesar Rodney | |||||
| 2012-13 | |||||
| 2011-12 | Smyrna | ||||
| 2010-11[26] | Polytech | Smyrna | Smyrna 46 – Polytech 41 | Smyrna | |
| 2009-10 | Polytech | Dover | Dover 71 – Polytech 55 | Dover[27] | |
| 2008-09 | Woodbridge | Caesar Rodney | Caesar Rodney 41 – Woodbridge 35 | Caesar Rodney | |
| 2007-08 | Woodbridge | Sussex Central | Woodbridge 71 – Sussex Central 60 | Woodbridge | |
| 2006-07 | |||||
| 2005-06 | Smyrna | Cape Henlopen | Cape Henlopen 77 – Smyrna 52 | Cape Henlopen | |
| 2004-05 | |||||
| 2003 | |||||
| 2002 | Lake Forest | Sussex Tech | Sussex Tech 58 – Lake Forest 48 | Sussex Tech | |
| 2001 | Lake Forest | Sussex Central | Sussex Central 59 – Lake Forest 49 | Sussex Central | |
| 2000 | Lake Forest | Sussex Tech | Sussex Tech 73 – Lake Forest 62 | Sussex Tech | |
| 1999 | Lake Forest | Sussex Tech | Sussex Tech 63 – Lake Forest 50 | Sussex Tech | |
| 1998 | Indian River | Cape Henlopen | Cape Henlopen 77 – Indian River 64 | Cape Henlopen | |
| 1997 | Lake Forest | Cape Henlopen | Lake Forest 49 – Cape Henlopen 45 | Lake Forest | |
| 1996 | Indian River | Cape Henlopen | Indian River 74 – Cape Henlopen 72 | Indian River | |
| 1995 | Indian River | Cape Henlopen | Indian River 52 – Cape Henlopen 51 | Indian River | |
| 1994 | Indian River | Caesar Rodney | Caesar Rodney 67 – Indian River 65 | Caesar Rodney | |
| 1993 | Indian River | Sussex Central | Indian River 58 – Sussex Central 45 | Indian River | |
| 1992 | Lake Forest | Dover | Dover 53 – Lake Forest 48 | Dover | |
| 1991 | Indian River | Seaford | Indian River 69 – Seaford 59 | Indian River | |
| 1990 | Indian River | Seaford | Indian River 65 – Seaford 63 | Indian River | |
| 1989 | Indian River | Milford | Milford 82 – Indian River 73 | Milford | |
| 1988 | Woodbridge | Seaford | Seaford 61 – Woodbridge 50 | Seaford | |
| 1987 | Woodbridge | Seaford | Seaford 77 – Woodbridge 63 | Seaford | |
| 1986 | Smyrna | Seaford | Seaford 74 – Smyrna 66 | Seaford | |
| 1985 | Smyrna | Sussex Central | Smyrna 64 – Sussex Central 55 | Smyrna | |
| 1984 | Seaford | Caesar Rodney | Caesar Rodney 61 – Seaford 60 | Caesar Rodney | |
| 1983 | Woodbridge | Cape Henlopen | Cape Henlopen 92 – Woodbridge 80 | Cape Henlopen | |
| 1982 | Lake Forest | Cape Henlopen | Cape Henlopen 71 – Lake Forest 57 | Cape Henlopen | |
| 1981 | Indian River | Cape Henlopen | Cape Henlopen 67 – Indian River 66 | Cape Henlopen | |
| 1980 | Indian River | Cape Henlopen | Cape Henlopen 77 – Indian River 63 | Cape Henlopen | |
| 1979 | Indian River | Cape Henlopen | Cape Henlopen 49 – Indian River 36 | Cape Henlopen | |
| 1978 | Indian River | Dover | Dover 55 – Indian River 53 | Dover | |
| 1977 | Indian River | Dover | Dover 61 – Indian River 59 | Dover | |
| 1976 | Indian River | Cape Henlopen | Cape Henlopen 78 – Indian River 57 | Cape Henlopen | |
| 1975 | Indian River | Cape Henlopen | Cape Henlopen 64 – Indian River 52 | Cape Henlopen | |
| 1974 | Indian River | Cape Henlopen | Indian River 66 – Cape Henlopen 62 | Indian River | |
| 1973 | Woodbridge | Cape Henlopen | Woodbridge 63 – Cape Henlopen 62 | Woodbridge | |
| 1972 | Indian River | Dover | Dover 69 – Indian River 53 | Dover | |
| 1971 | Indian River | Milford | Milford 47 – Indian River 45 | Milford | |
| 1970 | Lake Forest | Milford | Lake Forest 69 – Milford 43 | Lake Forest |
Prior to 1970 the conference was broken down into East and West based on geographic location. An Eastern Division and Western Division Champion was declared and a championship game was played between the two to determine the Henlopen Conference Champion. No division champions were declared in 1960 and 1961, instead the team with the best record was named Henlopen Conference Champion.
| Year | Henlopen West Division | Henlopen East Division | Conference Championship Game | Conference Champion | |
|---|---|---|---|---|---|
| 1969 | Dover Air Force Base | Rehoboth | Dover Air Force Base 77 – Rehoboth 70 | Dover Air Force Base | |
| 1968 | Bridgeville | Milton | Bridgeville 65 – Milton 58 | Bridgeville | |
| 1967 | Bridgeville | Milton | Milton 54 – Bridgeville 52 | Milton | |
| 1966 | Felton | Milton | Milton 60 – Felton 58 | Milton | |
| 1965 | Felton | Milton | Felton 73 – Milton 58 | Felton | |
| 1964 | Felton | Lord Baltimore | Felton 81 – Lord Baltimore 59 | Felton | |
| 1963 | Felton | Rehoboth | Rehoboth 48 – Felton 44 | Rehoboth | |
| 1962 | Greenwood | Milton | Milton 46 – Greenwood 38 | Milton | |
| 1961 | No Division Champion | No Division Champion | No Game | Rehoboth | |
| 1960 | No Division Champion | No Division Champion | No Game | Rehoboth |
Total Henlopen Conference Championships:
Caesar Rodney – 3 *Includes 1 won by Dover Air Force Base
Cape Henlopen – 15 *Includes 3 won by Rehoboth and 3 won by Milton
Delmar – 0
Dover – 4
Indian River – 6
Lake Forest – 4 *Includes 2 won by Felton
Laurel – 0
Milford – 2
Polytech – 0
Seaford – 3
Smyrna – 3
Sussex Central – 1
Sussex Tech – 3
Woodbridge – 2 *Includes 1 won by Bridgeville
| Year | Henlopen South Division | Henlopen North Division | Conference Champion |
|---|---|---|---|
| 2009 | Milford | Sussex Central | Sussex Central |
| 2008 | Indian River | Sussex Central | Indian River |
| 2007 | Indian River | Caesar Rodney | Caesar Rodney |
| 2006 | Indian River | Cape Henlopen | Cape Henlopen |
| 2005 | Indian River | Cape Henlopen | ???? |
| 2004 | Delmar | Caesar Rodney | Caesar Rodeny |
| 2003 | Laurel | Cape Henlopen | Cape Henlopen |
| 2002 | Seaford | Sussex Central | Seaford |
| 2001 | Seaford | Caesar Rodney | Caesar Rodney |
| 2000 | Laurel | Sussex Central |
The following Henlopen Conference boys teams have gone on to win state championships (includes pre-merger teams). Of note, if (I/II) appears in the division category, all divisions play for the only state championship.[28]
|
|
| Div I/Div II | School | Year | |
|---|---|---|---|
| II | Harrington Lions | 1963 | |
| II | Harrington Lions | 1966 | |
| II | Harrington Lions | 1969 | |
| II | Dover Air Force Base Falcons | 1971 | |
| II | Lake Forest Spartans | 1973 | |
| II | Lake Forest Spartans | 1974 | |
| II | Lake Forest Spartans | 1975 | |
| II | Lake Forest Spartans | 1976 | |
| II | Cape Henlopen Vikings | 1977 | |
| II | Woodbridge Blue Raiders | 1978 |
| Div I/Div II | School | Year | |
|---|---|---|---|
| II | Cape Henlopen Vikings | 1979 | |
| II | Sussex Central Golden Knights | 1980 | |
| II | Cape Henlopen Vikings | 1982 | |
| II | Lake Forest Spartans | 1983 | |
| II | Lake Forest Spartans | 1986 | |
| II | Lake Forest Spartans | 1992 | |
| II | Lake Forest Spartans | 1993 | |
| II | Lake Forest Spartans | 1996 | |
| II | Cape Henlopen Vikings | 1999 | |
| II | Cape Henlopen Vikings | 2001 |
| Div I/Div II | School | Year | |
|---|---|---|---|
| I | Caesar Rodney Riders | 1975 | |
| II | Delmar Wildcats | 1976 | |
| I | Dover Senators | 1977 | |
| I | Cape Henlopen Vikings | 1979 | |
| I | Seaford Blue Jays | 1981 | |
| II | Seaford Blue Jays | 1983 | |
| II | Delmar Wildcats | 1985 | |
| II | Laurel Bulldogs | 1986 | |
| II | Laurel Bulldogs | 1987 | |
| I | Dover Senators | 1988 |
| Div I/Div II | School | Year | |
|---|---|---|---|
| II | Indian River Indians | 1988 | |
| I | Caesar Rodney Riders | 1990 | |
| II | Laurel Bulldogs | 1991 | |
| II | Sussex Tech Ravens | 1993 | |
| II | Lake Forest Spartans | 1995 | |
| II | Delmar Wildcats | 2000 | |
| II | Delmar Wildcats | 2001 | |
| II | Delmar Wildcats | 2002 | |
| I | Caesar Rodney Riders | 2008 | |
| II | Milford Buccaneers | 2008 |
| Div I/Div II/Unified | School | Year | |
|---|---|---|---|
| II | Delmar Wildcats | 2009 | |
| II | Indian River Indians | 2011 | |
| I | Smyrna Eagles | 2015 | |
| I | Smyrna Eagles | 2016 | |
| II | Woodbridge Blue Raiders | 2016 | |
| I | Smyrna Eagles | 2017 | |
| II | Delmar Wildcats | 2017 | |
| I | Sussex Central Golden Knights | 2018 | |
| II | Woodbridge Blue Raiders | 2018 | |
| Unified | Smyrna Eagles | 2018 |
| Div I/Div II/Unified | School | Year | |
|---|---|---|---|
| Unified | Dover Senators | 2019 | |
| I | Sussex Central Golden Knights | 2020 |
| Div I/Div II | School | Year | |
|---|---|---|---|
| I/II | Dover Senators | 1985 | |
| I/II | Dover Senators | 1986 | |
| I/II | Dover Senators | 1988 | |
| I/II | Dover Senators | 1989 | |
| I/II | Caesar Rodney Riders | 1990 | |
| I/II | Dover Senators | 1991 | |
| I/II | Dover Senators | 1992 | |
| I/II | Dover Senators | 1993 | |
| I/II | Dover Senators | 1994 | |
| I/II | Dover Senators | 1995 |
| Div I/Div II | School | Year | |
|---|---|---|---|
| I/II | Dover Senators | 1996 | |
| I/II | Dover Senators | 1997 | |
| I/II | Caesar Rodney Riders | 1998 | |
| I/II | Dover Senators | 1999 | |
| I/II | Dover Senators | 2000 | |
| I/II | Dover Senators | 2003 | |
| I/II | Caesar Rodney Riders | 2011 | |
| I/II | Caesar Rodney Riders | 2012 | |
| I/II | Caesar Rodney Riders | 2013 |
|
|
| Div I/Div II | School | Year | |
|---|---|---|---|
| I | Seaford Blue Jays | 1965 | |
| I | Dover Senators | 1969 | |
| I | Cape Henlopen Vikings | 1971 | |
| I | Cape Henlopen Vikings | 1972 | |
| I | Cape Henlopen Vikings | 1973 | |
| I | Cape Henlopen Vikings | 1975 | |
| I | Dover Senators | 1975 | |
| II | Cape Henlopen Vikings | 1976 | |
| I | Dover Senators | 1976 | |
| I** | Dover Senators | 1977 |
| Div I/Div II | School | Year | |
|---|---|---|---|
| II** | Seaford Blue Jays | 1977 | |
| II | Cape Henlopen Vikings | 1978 | |
| II | Woodbridge Blue Raiders | 1979 | |
| I | Dover Senators | 1980 | |
| II | Woodbridge Blue Raiders | 1981 | |
| II | Woodbridge Blue Raiders | 1982 | |
| II | Lake Forest Spartans | 1984 | |
| I | Cape Henlopen Vikings | 1986 | |
| II | Milford Buccaneers | 1986 | |
| II | Lake Forest Spartans | 1987 |
| Div I/Div II | School | Year | |
|---|---|---|---|
| II | Smyrna Eagles | 1990 | |
| II | Smyrna Eagles | 1991 | |
| II | Cape Henlopen Vikings | 1992 | |
| II | Cape Henlopen Vikings | 1993 | |
| I | Dover Senators | 1995 | |
| II | Cape Henlopen Vikings | 2000 | |
| II | Cape Henlopen Vikings | 2002 | |
| I | Dover Senators | 2004 | |
| II | Milford Buccaneers | 2005 | |
| II | Milford Buccaneers | 2009 |
| Div I/Div II/Unified | School | Year | |
|---|---|---|---|
| II | Milford Buccaneers | 2011 | |
| I | Caesar Rodney Riders | 2013 | |
| I | Caesar Rodney Riders | 2014 | |
| I | Dover Senators | 2015 | |
| II | Lake Forest Spartans | 2015 | |
| Unified | Smyrna Eagles | 2016 | |
| I | Dover Senators | 2017 | |
| Unified | Caesar Rodney Riders | 2017 | |
| I | Dover Senators | 2018 | |
| Unified | Caesar Rodney Riders | 2018 |
|
|
| Div I/Div II | School | Year | |
|---|---|---|---|
| I/II | Caesar Rodney Riders | 1975 | |
| I/II | Caesar Rodney Riders | 1978 | |
| I/II | Caesar Rodney Riders | 1979 | |
| I/II | Milford Buccaneers | 1980 | |
| I/II | Milford Buccaneers | 1981 | |
| I/II | Caesar Rodney Riders | 1982 | |
| I/II | Caesar Rodney Riders | 1985 | |
| II | Smyrna Eagles | 1993 | |
| II | Smyrna Eagles | 1994 | |
| II | Smyrna Eagles | 1996 |
| Div I/Div II | School | Year | |
|---|---|---|---|
| I | Caesar Rodney Riders | 2001 | |
| I | Caesar Rodney Riders | 2003 | |
| II | Smyrna Eagles | 2003 | |
| I | Caesar Rodney Riders | 2004 | |
| II | Milford Buccaneers | 2004 | |
| I | Caesar Rodney Riders | 2005 | |
| II | Smyrna Eagles | 2005 | |
| I | Caesar Rodney Riders | 2006 | |
| I | Caesar Rodney Riders | 2007 | |
| I | Sussex Central Golden Knights | 2008 |
| Div I/Div II | School | Year | |
|---|---|---|---|
| II | Milford Buccaneers | 2009 | |
| I | Sussex Central Golden Knights | 2010 | |
| I | Caesar Rodney Riders | 2011 | |
| I | Caesar Rodney Riders | 2012 | |
| II | Polytech Panthers | 2012 | |
| I | Smyrna Eagles | 2013 | |
| I | Smyrna Eagles | 2014 | |
| II | Milford Buccaneers | 2014 | |
| I | Smyrna Eagles | 2015 | |
| II | Milford Buccaneers | 2015 |
| Div I/Div II | School | Year | |
|---|---|---|---|
| I | Smyrna Eagles | 2016 | |
| II | Milford Buccaneers | 2016 | |
| I | Sussex Central Golden Knights | 2017 | |
| II | Milford Buccaneers | 2017 | |
| I | Caesar Rodney Riders | 2018 | |
| II | Milford Buccaneers | 2018 | |
| I | Smyrna Eagles | 2019 | |
| II | Milford Buccaneers | 2019 | |
| I | Smyrna Eagles | 2020 | |
| I | Cape Henlopen Vikings | 2021 |
|
The following Henlopen Conference girl teams have gone on to win state championships (includes pre-merger teams). Of note, if (I/II) appears in the division category, all divisions play for the only state championship. There were no girls championships until the 1973–1974 school year, all championships are post-merger.[28]
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The total number of state championships won by Henlopen Conference teams in both boys and girls sports, in order of championships won:
Cape Henlopen Vikings – 54
Caesar Rodney Riders – 48
Dover Senators – 37
Lake Forest Spartans – 22
Milford Buccaneers – 21
Seaford Blue Jays – 16
Smyrna Eagles – 15
Sussex Central Golden Knights – 10
Delmar Wildcats – 7
Indian River Indians – 7
Woodbridge Blue Raiders – 6
Laurel Bulldogs – 5
Sussex Tech Ravens – 5
Polytech Panthers – 3
Dover Air Force Base (defunct) – 1
[32]