Elections are currently held every four years to elect the mayor of Chesapeake, Virginia.
| Election Name: | 2004 Chesapeake mayoral election |
| Type: | mayoral |
| Ongoing: | no |
| Previous Year: | 2000 |
| Next Year: | 2008 |
| Candidate1: | William Ward |
| Party1: | Independent |
| Popular Vote1: | 13,633 |
| Percentage1: | 51.40% |
| Candidate2: | W. Joe Newman |
| Party2: | Independent |
| Popular Vote2: | 12,505 |
| Percentage2: | 47.15% |
| Mayor | |
| Before Election: | William Ward |
| Before Party: | Independent |
| After Election: | William Ward |
| After Party: | Independent |
| Candidate3: | James Walz |
| Party3: | Independent |
| Popular Vote3: | 252 |
| Percentage3: | 0.95% |
The 2004 Chesapeake mayoral election was held on May 4, 2004. It saw the reelection of the incumbent mayor William E. Ward.
| Election Name: | 2008 Chesapeake mayoral election |
| Type: | mayoral |
| Ongoing: | no |
| Previous Year: | 2004 |
| Next Year: | 2012 |
| Candidate1: | Alan Krasnoff |
| Party1: | Independent |
| Popular Vote1: | 12,546 |
| Percentage1: | 53.46% |
| Candidate2: | Rebecca Adams |
| Party2: | Independent |
| Popular Vote2: | 10,886 |
| Percentage2: | 46.38% |
| Mayor | |
| Before Election: | Dalton Edge |
| Before Party: | Independent |
| After Election: | Alan Krasnoff |
| After Party: | Independent |
The 2008 Chesapeake mayoral election was held on May 6, 2008. It saw the election of Alan Krasnoff, a member of the city council.[1]
| Election Name: | 2012 Chesapeake mayoral election |
| Type: | mayoral |
| Ongoing: | no |
| Previous Year: | 2008 |
| Next Year: | 2016 |
| Candidate1: | Alan Krasnoff |
| Party1: | Independent |
| Popular Vote1: | 12,578 |
| Percentage1: | 74.27% |
| Candidate2: | Burnie Mansfield Jr. |
| Party2: | Independent |
| Popular Vote2: | 3,327 |
| Percentage2: | 19.64% |
| Mayor | |
| Before Election: | Alan Krasnoff |
| Before Party: | Independent |
| After Election: | Alan Krasnoff |
| After Party: | Independent |
| Candidate3: | Harrietta Gibbons |
| Party3: | Independent |
| Popular Vote3: | 935 |
| Percentage3: | 5.52% |
The 2012 Chesapeake mayoral election was held on May 1, 2012. The incumbent mayor Alan Krasnoff won a second term to his mayoral office.[2]
The 2016 Chesapeake mayoral election was held on May 3, 2016. The incumbent mayor Alan Krasnoff won by default due to the lack of opposing candidates.[3]
| Election Name: | 2018 Chesapeake special mayoral election |
| Type: | mayoral |
| Ongoing: | no |
| Previous Year: | 2016 |
| Next Year: | 2020 |
| Candidate1: | Richard West |
| Party1: | Independent |
| Popular Vote1: | 13,342 |
| Percentage1: | 57.81% |
| Candidate2: | Jo Anne Gallant |
| Party2: | Independent |
| Popular Vote2: | 9,630 |
| Percentage2: | 41.72% |
| Mayor | |
| Before Election: | Alan Krasnoff |
| Before Party: | Independent |
| After Election: | Richard West |
| After Party: | Independent |
On the municipal election of Chesapeake in November 2017, the incumbent mayor Alan Krasnoff ran for and won the election was the Chesapeake City Clerk of Court. Since Krasnoff left the post of mayor on November 14, Richard West, a city council member, became the acting mayor.[4] A special mayoral election was held on May 1, 2018. It saw the election of the acting mayor Richard West.[5]
| Election Name: | 2020 Chesapeake mayoral election |
| Type: | mayoral |
| Ongoing: | no |
| Previous Year: | 2018 |
| Next Year: | 2024 |
| Candidate1: | Richard West |
| Party1: | Independent |
| Popular Vote1: | 21,888 |
| Percentage1: | 65.94% |
| Candidate2: | Lenard Myers II |
| Party2: | Independent |
| Popular Vote2: | 9,087 |
| Percentage2: | 27.38% |
| Mayor | |
| Before Election: | Richard West |
| Before Party: | Independent |
| After Election: | Richard West |
| After Party: | Independent |
| Candidate4: | Steffanie Aubuchon |
| Party4: | Independent |
| Popular Vote4: | 1,386 |
| Percentage4: | 4.18% |
| Candidate5: | Palmer Smith |
| Party5: | Independent |
| Popular Vote5: | 641 |
| Percentage5: | 1.93% |
The 2020 Chesapeake mayoral election was held on May 19, 2020. It saw the reelection of the incumbent mayor Richard West.[6]
The following served as mayors of Chesapeake: