17‑Nov‑1986 | Houston | Carpet | R16 | 79 | 61 | Scott Davis [USA] d. Holmes | 7-6 6-3 | | | | | | | | | |
17‑Nov‑1986 | Houston | Carpet | R32 | 79 | 187 | Holmes d. Martin Wostenholme [CAN] | 4-6 7-6 6-0 | | | | | | | | | |
27‑Oct‑1986 | Hong Kong | Hard | R32 | 72 | 34 | (5)Andrei Chesnokov [RUS] d. Holmes | 6-4 6-2 | | | | | | | | | |
20‑Oct‑1986 | Tokyo Indoor | Carpet | R32 | 74 | 52 | Jaime Yzaga [PER] d. Holmes | 6-4 6-4 | | | | | | | | | |
13‑Oct‑1986 | Tokyo Outdoor | Hard | R32 | 69 | 264 | Paul Chamberlin [USA] d. (10)Holmes | 4-6 7-5 7-6 | | | | | | | | | |
13‑Oct‑1986 | Tokyo Outdoor | Hard | R64 | 69 | 855 | (10)Holmes d. (WC)Kazuya Morita [JPN] | 6-1 6-1 | | | | | | | | | |
22‑Sep‑1986 | San Francisco | Carpet | R32 | 61 | 189 | (WC)Peter Fleming [USA] d. Holmes | 6-2 6-4 | | | | | | | | | |
26‑Aug‑1986 | US Open | Hard | R128 | 42 | 176 | (WC)Tom Gullikson [USA] d. Holmes | 7-6 7-6 6-7 0-6 7-6 | | | | | | | | | |
18‑Aug‑1986 | Cincinnati | Hard | R32 | 46 | 11 | (5)Mikael Pernfors [SWE] d. Holmes | 6-2 6-7 6-4 | | | | | | | | | |
18‑Aug‑1986 | Cincinnati | Hard | R64 | 46 | 72 | Holmes d. Todd Witsken [USA] | 7-5 6-7 6-2 | | | | | | | | | |
11‑Aug‑1986 | Montreal / Toronto | Hard | R32 | 43 | 1 | (1)Ivan Lendl [USA] d. Holmes | 6-2 6-2 | | | | | | | | | |
11‑Aug‑1986 | Montreal / Toronto | Hard | R64 | 43 | 230 | Holmes d. (Q)Bill Cowan [CAN] | 6-2 6-2 | | | | | | | | | |
4‑Aug‑1986 | Stratton Mountain | Hard | R16 | 55 | 14 | (7)Brad Gilbert [USA] d. Holmes | 6-2 4-6 6-2 | | | | | | | | | |
4‑Aug‑1986 | Stratton Mountain | Hard | R32 | 55 | 17 | Holmes d. (9)Johan Kriek [USA] | 6-1 6-3 | | | | | | | | | |
4‑Aug‑1986 | Stratton Mountain | Hard | R64 | 55 | 44 | Holmes d. Eddie Edwards [RSA] | 6-4 6-2 | | | | | | | | | |
21‑Jul‑1986 | Livingston | Hard | QF | 52 | 80 | Mike Leach [USA] d. (7)Holmes | 4-6 7-6 6-4 | | | | | | | | | |
21‑Jul‑1986 | Livingston | Hard | R16 | 52 | 422 | (7)Holmes d. (LL)Howard Herr [RSA] | 4-6 6-4 6-0 | | | | | | | | | |
21‑Jul‑1986 | Livingston | Hard | R32 | 52 | 70 | (7)Holmes d. Marcel Freeman [USA] | 6-4 6-3 | | | | | | | | | |
23‑Jun‑1986 | Wimbledon | Grass | R32 | 48 | 9 | (7)Henri Leconte [FRA] d. Holmes | 6-4 6-2 7-6 | | | | | | | | | |
23‑Jun‑1986 | Wimbledon | Grass | R64 | 48 | 90 | Holmes d. Michael Westphal [GER] | 3-6 7-6 7-5 4-6 6-2 | | | | | | | | | |
23‑Jun‑1986 | Wimbledon | Grass | R128 | 48 | 80 | Holmes d. Ricardo Acuna [CHI] | 6-3 7-6 6-4 | | | | | | | | | |
9‑Jun‑1986 | Queen's Club | Grass | R64 | 46 | 30 | (16)Guy Forget [FRA] d. Holmes | 6-1 RET | | | | | | | | | |
17‑Mar‑1986 | Fort Myers | Hard | QF | 80 | 17 | (6)Tim Mayotte [USA] d. Holmes | 3-6 6-3 7-6 | | | | | | | | | |
17‑Mar‑1986 | Fort Myers | Hard | R16 | 80 | 79 | Holmes d. (Q)Ken Flach [USA] | 6-3 6-2 | | | | | | | | | |
17‑Mar‑1986 | Fort Myers | Hard | R32 | 80 | 11 | Holmes d. (3)Brad Gilbert [USA] | 6-2 6-4 | | | | | | | | | |
24‑Feb‑1986 | La Quinta | Hard | R64 | 81 | 287 | (WC)Brad Pearce [USA] d. Holmes | 7-6 6-3 | | | | | | | | | |
10‑Feb‑1986 | Boca West | Hard | R32 | 34 | 1 | (1)Ivan Lendl [USA] d. (32)Holmes | 6-4 7-6 | | | | | | | | | |
10‑Feb‑1986 | Boca West | Hard | R64 | 34 | 109 | (32)Holmes d. Bob Green [USA] | 6-3 6-4 | | | | | | | | | |
10‑Feb‑1986 | Boca West | Hard | R128 | 34 | 82 | (32)Holmes d. Horacio De La Pena [ARG] | 7-6 6-4 | | | | | | | | | |
3‑Feb‑1986 | Memphis | Carpet | R16 | 37 | 8 | (3)Anders Jarryd [SWE] d. (14)Holmes | 6-4 7-6 | | | | | | | | | |
3‑Feb‑1986 | Memphis | Carpet | R32 | 37 | 247 | (14)Holmes d. (WC)Steve Denton [USA] | 6-4 3-6 7-6 | | | | | | | | | |
27‑Jan‑1986 | Philadelphia | Carpet | R16 | 27 | 1 | (1)Ivan Lendl [USA] d. (16)Holmes | 6-2 6-2 | | | | | | | | | |
27‑Jan‑1986 | Philadelphia | Carpet | R32 | 27 | 34 | (16)Holmes d. Libor Pimek [BEL] | 6-2 6-4 | | | | | | | | | |