These are the number-one singles of 1986 according to the Top 100 Singles chart in Cash Box magazine.
| Indicates best-performing single of 1986 |
| Issue date | Song | Artist | |
|---|---|---|---|
| January 4 | "Say You, Say Me" | ||
| January 11 | |||
| January 18 | |||
| January 25 | "That's What Friends Are For" | Dionne Warwick & Friends | |
| February 1 | |||
| February 8 | |||
| February 15 | "When the Going Gets Tough, the Tough Get Going" | Billy Ocean | |
| February 22 | "How Will I Know" | Whitney Houston | |
| March 1 | "Kyrie" | ||
| March 8 | |||
| March 15 | "Sara" | ||
| March 22 | "These Dreams" | Heart | |
| March 29 | "Rock Me Amadeus" | Falco | |
| April 5 | |||
| April 12 | "Kiss" | Prince & Revolution | |
| April 19 | |||
| April 26 | "Addicted To Love" | Robert Palmer | |
| May 3 | |||
| May 10 | "West End Girls" | Pet Shop Boys | |
| May 17 | "Why Can't This Be Love" | Van Halen | |
| May 24 | "Greatest Love Of All" | ||
| May 31 | |||
| June 7 | "Live to Tell" | Madonna | |
| June 14 | "On My Own" | Patti LaBelle & Michael McDonald | |
| June 21 | |||
| June 28 | |||
| July 5 | "There'll Be Sad Songs (To Make You Cry)" | Billy Ocean | |
| July 12 | |||
| July 19 | "Invisible Touch" | ||
| July 26 | "Sledgehammer" | Peter Gabriel | |
| August 2 | |||
| August 9 | "Glory of Love" | Peter Cetera | |
| August 16 | "Papa Don't Preach" | Madonna | |
| August 23 | |||
| August 30 | bgcolor=#FFFF99 rowspan="2" | "Higher Love" | Steve Winwood |
| September 6 | |||
| September 13 | "Take My Breath Away" | ||
| September 20 | "Stuck with You" | Huey Lewis and the News | |
| September 27 | |||
| October 4 | |||
| October 11 | "When I Think Of You" | ||
| October 18 | |||
| October 25 | "Typical Male" | Tina Turner | |
| November 1 | "True Colors" | Cyndi Lauper | |
| November 8 | "Amanda" | Boston | |
| November 15 | |||
| November 22 | |||
| November 29 | "Human" | ||
| December 6 | "You Give Love A Bad Name" | Bon Jovi | |
| December 13 | "The Way It Is" | ||
| December 20 | "Walk Like an Egyptian" | ||
| December 27 | "Everybody Have Fun Tonight" |