3‑Nov‑1986 | Stockholm | Hard | R32 | 32 | 113 | Ben Testerman [USA] d. (11)Wilkison | 3-6 4-3 RET | | | | | | | | | |
3‑Nov‑1986 | Stockholm | Hard | R64 | 32 | 70 | (11)Wilkison d. Libor Pimek [BEL] | 4-6 7-6 6-4 | | | | | | | | | |
27‑Oct‑1986 | Paris Indoor | Carpet | R32 | 31 | 37 | Karel Novacek [CZE] d. Wilkison | 6-1 5-7 6-4 | | | | | | | | | |
20‑Oct‑1986 | Vienna | Hard | R32 | 29 | 149 | Ricki Osterthun [GER] d. (4)Wilkison | 7-5 6-1 | | | | | | | | | |
13‑Oct‑1986 | Basel | Hard | R32 | 26 | 67 | Tomas Smid [CZE] d. (4)Wilkison | 6-3 3-6 6-4 | | | | | | | | | |
6‑Oct‑1986 | Toulouse | Hard | R32 | 23 | 72 | Michiel Schapers [NED] d. (3)Wilkison | 6-3 7-6 | | | | | | | | | |
26‑Aug‑1986 | US Open | Hard | QF | 31 | 4 | (4)Stefan Edberg [SWE] d. Wilkison | 6-3 6-3 6-3 | | | | | | | | | |
26‑Aug‑1986 | US Open | Hard | R16 | 31 | 46 | Wilkison d. Andrei Chesnokov [RUS] | 6-0 6-2 6-3 | | | | | | | | | |
26‑Aug‑1986 | US Open | Hard | R32 | 31 | 6 | Wilkison d. (5)Yannick Noah [FRA] | 7-6 3-6 4-6 6-1 6-4 | | | | | | | | | |
26‑Aug‑1986 | US Open | Hard | R64 | 31 | 43 | Wilkison d. Paul Mcnamee [AUS] | 6-1 6-2 6-1 | | | | | | | | | |
26‑Aug‑1986 | US Open | Hard | R128 | 31 | 75 | Wilkison d. Horst Skoff [AUT] | 7-6 6-2 6-0 | | | | | | | | | |
18‑Aug‑1986 | Cincinnati | Hard | QF | 28 | 4 | (3)Stefan Edberg [SWE] d. (12)Wilkison | 7-6 7-6 | | | | | | | | | |
18‑Aug‑1986 | Cincinnati | Hard | R16 | 28 | 53 | (12)Wilkison d. Jonas Svensson [SWE] | 6-4 6-2 | | | | | | | | | |
18‑Aug‑1986 | Cincinnati | Hard | R32 | 28 | 84 | (12)Wilkison d. Jimmy Brown [USA] | 7-6 6-2 | | | | | | | | | |
18‑Aug‑1986 | Cincinnati | Hard | R64 | 28 | 111 | (12)Wilkison d. Hans Schwaier [GER] | 6-3 6-2 | | | | | | | | | |
11‑Aug‑1986 | Montreal / Toronto | Hard | R16 | 28 | 6 | (4)Stefan Edberg [SWE] d. (13)Wilkison | 6-3 6-4 | | | | | | | | | |
11‑Aug‑1986 | Montreal / Toronto | Hard | R32 | 28 | 84 | (13)Wilkison d. Vijay Amritraj [IND] | 6-7 2-1 RET | | | | | | | | | |
11‑Aug‑1986 | Montreal / Toronto | Hard | R64 | 28 | 38 | (13)Wilkison d. Guy Forget [FRA] | 6-3 5-7 6-3 | | | | | | | | | |
4‑Aug‑1986 | Stratton Mountain | Hard | R32 | 29 | 66 | Pablo Arraya [PER] d. (13)Wilkison | 6-4 4-6 6-2 | | | | | | | | | |
4‑Aug‑1986 | Stratton Mountain | Hard | R64 | 29 | 68 | (13)Wilkison d. Glenn Michibata [CAN] | 4-6 6-4 6-1 | | | | | | | | | |
7‑Jul‑1986 | Newport | Grass | F | 32 | 151 | Bill Scanlon [USA] d. (2)Wilkison | 7-5 6-4 | | | | | | | | | |
7‑Jul‑1986 | Newport | Grass | SF | 32 | 55 | (2)Wilkison d. Eddie Edwards [RSA] | 6-3 7-6 | | | | | | | | | |
7‑Jul‑1986 | Newport | Grass | QF | 32 | 105 | (2)Wilkison d. Vallis Wilder [USA] | 7-5 6-2 | | | | | | | | | |
7‑Jul‑1986 | Newport | Grass | R16 | 32 | 154 | (2)Wilkison d. Brad Drewett [AUS] | 6-7 6-3 6-2 | | | | | | | | | |
7‑Jul‑1986 | Newport | Grass | R32 | 32 | 189 | (2)Wilkison d. (LL)Brett Dickinson [USA] | 6-2 6-3 | | | | | | | | | |
23‑Jun‑1986 | Wimbledon | Grass | R64 | 28 | 214 | (Q)Christo Van Rensburg [RSA] d. Wilkison | 6-4 6-2 6-1 | | | | | | | | | |
23‑Jun‑1986 | Wimbledon | Grass | R128 | 28 | 226 | Wilkison d. (WC)Steve Shaw [GBR] | 7-5 6-7 6-4 6-4 | | | | | | | | | |
16‑Jun‑1986 | Bristol | Grass | QF | 29 | 104 | (WC)Vijay Amritraj [IND] d. (2)Wilkison | 6-4 6-4 | | | | | | | | | |
16‑Jun‑1986 | Bristol | Grass | R16 | 29 | 122 | (2)Wilkison d. Darren Cahill [AUS] | 6-1 6-7 7-5 | | | | | | | | | |
16‑Jun‑1986 | Bristol | Grass | R32 | 29 | 714 | (2)Wilkison d. (Q)James Turner [GBR] | 7-6 6-1 | | | | | | | | | |
9‑Jun‑1986 | Queen's Club | Grass | QF | 31 | 7 | (3)Stefan Edberg [SWE] d. (12)Wilkison | 6-3 6-3 | | | | | | | | | |
9‑Jun‑1986 | Queen's Club | Grass | R16 | 31 | 77 | (12)Wilkison d. Todd Nelson [USA] | 6-7 7-6 13-11 | | | | | | | | | |
9‑Jun‑1986 | Queen's Club | Grass | R32 | 31 | 91 | (12)Wilkison d. Bob Green [USA] | 7-6 6-0 | | | | | | | | | |
9‑Jun‑1986 | Queen's Club | Grass | R64 | 31 | 217 | (12)Wilkison d. (WC)Steve Shaw [GBR] | 6-3 6-2 | | | | | | | | | |
26‑May‑1986 | Roland Garros | Clay | R128 | 28 | 73 | Thomas Muster [AUT] d. Wilkison | 6-3 6-4 6-3 | | | | | | | | | |
5‑May‑1986 | Forest Hills | Clay | R16 | 31 | 8 | (3)Joakim Nystrom [SWE] d. (14)Wilkison | 6-3 6-7 6-2 | | | | | | | | | |
5‑May‑1986 | Forest Hills | Clay | R32 | 31 | 99 | (14)Wilkison d. Harold Solomon [USA] | 6-2 1-6 6-2 | | | | | | | | | |
5‑May‑1986 | Forest Hills | Clay | R64 | 31 | 116 | (14)Wilkison d. Roberto Arguello [ARG] | 6-2 6-1 | | | | | | | | | |
28‑Apr‑1986 | Indianapolis | Clay | R16 | 29 | 108 | Eduardo Bengoechea [ARG] d. (7)Wilkison | 6-3 7-6 | | | | | | | | | |
28‑Apr‑1986 | Indianapolis | Clay | R32 | 29 | 67 | (7)Wilkison d. Pablo Arraya [PER] | 6-1 6-3 | | | | | | | | | |
31‑Mar‑1986 | Atlanta | Carpet | F | 46 | 12 | (4)Kevin Curren [USA] d. Wilkison | 7-6 7-6 | | | | | | | | | |
31‑Mar‑1986 | Atlanta | Carpet | SF | 46 | 26 | Wilkison d. David Pate [USA] | 6-4 2-6 6-4 | | | | | | | | | |
31‑Mar‑1986 | Atlanta | Carpet | QF | 46 | 62 | Wilkison d. Mike Leach [USA] | 6-1 7-6 | | | | | | | | | |
31‑Mar‑1986 | Atlanta | Carpet | R16 | 46 | 52 | Wilkison d. Glenn Michibata [CAN] | 6-1 6-2 | | | | | | | | | |
31‑Mar‑1986 | Atlanta | Carpet | R32 | 46 | 5 | Wilkison d. (2)Boris Becker [GER] | 6-2 2-6 6-1 | | | | | | | | | |
24‑Mar‑1986 | Chicago | Carpet | R32 | 41 | 1 | (1)Ivan Lendl [USA] d. Wilkison | 6-4 6-3 | | | | | | | | | |
17‑Mar‑1986 | Fort Myers | Hard | R32 | 34 | 15 | (4)Johan Kriek [USA] d. Wilkison | 6-4 6-3 | | | | | | | | | |
24‑Feb‑1986 | La Quinta | Hard | R32 | 38 | 7 | (4)Yannick Noah [FRA] d. Wilkison | 6-4 6-4 | | | | | | | | | |
24‑Feb‑1986 | La Quinta | Hard | R64 | 38 | 42 | Wilkison d. Hans Schwaier [GER] | 7-5 6-1 | | | | | | | | | |
10‑Feb‑1986 | Boca West | Hard | R32 | 41 | 7 | (6)Yannick Noah [FRA] d. Wilkison | 6-4 1-6 6-3 | | | | | | | | | |
10‑Feb‑1986 | Boca West | Hard | R64 | 41 | 229 | Wilkison d. Mel Purcell [USA] | 6-4 6-3 | | | | | | | | | |
10‑Feb‑1986 | Boca West | Hard | R128 | 41 | 128 | Wilkison d. Barry Moir [RSA] | 6-3 6-3 | | | | | | | | | |
3‑Feb‑1986 | Memphis | Carpet | R32 | 40 | 8 | (3)Anders Jarryd [SWE] d. Wilkison | 6-2 6-4 | | | | | | | | | |
3‑Feb‑1986 | Memphis | Carpet | R64 | 40 | 60 | Wilkison d. Ricardo Acuna [CHI] | 6-3 6-0 | | | | | | | | | |
27‑Jan‑1986 | Philadelphia | Carpet | R32 | 44 | 10 | (6)Kevin Curren [USA] d. Wilkison | 7-5 6-2 | | | | | | | | | |
27‑Jan‑1986 | Philadelphia | Carpet | R64 | 44 | 204 | Wilkison d. (Q)Tomm Warneke [USA] | 7-6 7-6 | | | | | | | | | |