24‑Oct‑1988 | Paris Indoor | Carpet | R32 | 26 | 20 | Aaron Krickstein [USA] d. Cahill | 7-6 7-6 | | | | | | | | | |
18‑Oct‑1988 | Tokyo Indoor | Carpet | R32 | 26 | 99 | (WC)Shuzo Matsuoka [JPN] d. (4)Cahill | 7-6 6-1 | | | | | | | | | |
10‑Oct‑1988 | Sydney Indoor | Hard | R16 | 26 | 154 | Grant Connell [CAN] d. (3)Cahill | 3-6 7-6 6-2 | | | | | | | | | |
10‑Oct‑1988 | Sydney Indoor | Hard | R32 | 26 | 265 | (3)Cahill d. (WC)Todd Woodbridge [AUS] | 6-4 6-4 | | | | | | | | | |
4‑Oct‑1988 | Brisbane | Hard | R32 | 25 | 197 | (WC)Shane Barr [AUS] d. (2)Cahill | 6-2 6-1 | | | | | | | | | |
20‑Sep‑1988 | Seoul Olympics | Hard | R32 | 23 | 52 | (LL)Robert Seguso [USA] d. (9)Cahill | 6-3 7-6 6-7 6-2 | | | | | | | | | |
20‑Sep‑1988 | Seoul Olympics | Hard | R64 | 23 | 187 | (9)Cahill d. (Q)Alex Antonitsch [AUT] | 6-2 6-4 6-7 6-2 | | | | | | | | | |
29‑Aug‑1988 | US Open | Hard | SF | 33 | 2 | (2)Mats Wilander [SWE] d. Cahill | 6-4 6-4 6-2 | (ch) | | | | | | | | |
29‑Aug‑1988 | US Open | Hard | QF | 33 | 20 | Cahill d. Aaron Krickstein [USA] | 6-2 5-7 7-6 5-7 6-3 | | | | | | | | | |
29‑Aug‑1988 | US Open | Hard | R16 | 33 | 151 | Cahill d. (Q)Martin Laurendeau [CAN] | 6-4 6-4 6-3 | | | | | | | | | |
29‑Aug‑1988 | US Open | Hard | R32 | 33 | 104 | Cahill d. Marcelo Ingaramo [ARG] | W/O | | | | | | | | | |
29‑Aug‑1988 | US Open | Hard | R64 | 33 | 5 | Cahill d. (5)Boris Becker [GER] | 6-3 6-3 6-2 | | | | | | | | | |
29‑Aug‑1988 | US Open | Hard | R128 | 33 | 55 | Cahill d. Lawson Duncan [USA] | 6-0 6-0 6-2 | | | | | | | | | |
15‑Aug‑1988 | Cincinnati | Hard | R64 | 33 | 50 | Wally Masur [AUS] d. (16)Cahill | 3-6 6-3 6-1 | | | | | | | | | |
25‑Jul‑1988 | Stratton Mountain | Hard | SF | 35 | 48 | (13)Paul Annacone [USA] d. (9)Cahill | 6-4 6-3 | | | | | | | | | |
25‑Jul‑1988 | Stratton Mountain | Hard | QF | 35 | 150 | (9)Cahill d. Roger Smith [BAH] | 6-3 4-6 6-2 | | | | | | | | | |
25‑Jul‑1988 | Stratton Mountain | Hard | R16 | 35 | 183 | (9)Cahill d. Michael Robertson [USA] | 6-2 6-7 6-2 | | | | | | | | | |
25‑Jul‑1988 | Stratton Mountain | Hard | R32 | 35 | 181 | (9)Cahill d. Dan Cassidy [USA] | 6-1 6-2 | | | | | | | | | |
25‑Jul‑1988 | Stratton Mountain | Hard | R64 | 35 | 67 | (9)Cahill d. Kelly Evernden [NZL] | 6-3 6-0 | | | | | | | | | |
18‑Jul‑1988 | Washington | Hard | QF | 36 | 82 | (16)Derrick Rostagno [USA] d. (7)Cahill | 6-4 7-6 | | | | | | | | | |
18‑Jul‑1988 | Washington | Hard | R16 | 36 | 98 | (7)Cahill d. Chris Pridham [CAN] | 6-2 6-1 | | | | | | | | | |
18‑Jul‑1988 | Washington | Hard | R32 | 36 | 515 | (7)Cahill d. (Q)Brian Page [USA] | 6-3 6-3 | | | | | | | | | |
11‑Jul‑1988 | Stuttgart Outdoor | Clay | R32 | 35 | 9 | (3)Brad Gilbert [USA] d. Cahill | 6-4 7-6 | | | | | | | | | |
11‑Jul‑1988 | Stuttgart Outdoor | Clay | R64 | 35 | 91 | Cahill d. Guillermo Vilas [ARG] | 6-3 1-6 6-3 | | | | | | | | | |
4‑Jul‑1988 | Gstaad | Clay | F | 45 | 43 | Cahill d. (7)Jakob Hlasek [SUI] | 6-3 6-4 7-6 | | | | | | | | | |
4‑Jul‑1988 | Gstaad | Clay | SF | 45 | 75 | Cahill d. Horst Skoff [AUT] | 6-1 6-1 | | | | | | | | | |
4‑Jul‑1988 | Gstaad | Clay | QF | 45 | 15 | Cahill d. (2)Emilio Sanchez [ESP] | 4-6 7-6 7-6 | | | | | | | | | |
4‑Jul‑1988 | Gstaad | Clay | R16 | 45 | 38 | Cahill d. (8)Tomas Smid [CZE] | 6-1 6-4 | | | | | | | | | |
4‑Jul‑1988 | Gstaad | Clay | R32 | 45 | 445 | Cahill d. (Q)Marko Ostoja [CRO] | 6-4 6-2 | | | | | | | | | |
20‑Jun‑1988 | Wimbledon | Grass | R64 | 47 | 1 | (1)Ivan Lendl [USA] d. Cahill | 5-7 6-2 6-4 6-4 | | | | | | | | | |
20‑Jun‑1988 | Wimbledon | Grass | R128 | 47 | 107 | Cahill d. Gary Muller [RSA] | 6-7 6-2 6-2 6-0 | | | | | | | | | |
6‑Jun‑1988 | Queen's Club | Grass | SF | 66 | 7 | (4)Boris Becker [GER] d. Cahill | 6-2 6-4 | | | | | | | | | |
6‑Jun‑1988 | Queen's Club | Grass | QF | 66 | 30 | Cahill d. (9)Kevin Curren [USA] | 7-5 7-6 | | | | | | | | | |
6‑Jun‑1988 | Queen's Club | Grass | R16 | 66 | 4 | Cahill d. (2)Pat Cash [AUS] | 7-6 6-4 | | | | | | | | | |
6‑Jun‑1988 | Queen's Club | Grass | R32 | 66 | 88 | Cahill d. Ken Flach [USA] | 2-6 7-5 6-3 | | | | | | | | | |
6‑Jun‑1988 | Queen's Club | Grass | R64 | 66 | 230 | Cahill d. (Q)Ricardo Acuna [CHI] | 6-7 6-3 9-7 | | | | | | | | | |
23‑May‑1988 | Roland Garros | Clay | R128 | 63 | 54 | Eduardo Bengoechea [ARG] d. Cahill | 6-7 7-6 5-7 6-2 6-3 | | | | | | | | | |
2‑May‑1988 | Munich | Clay | R32 | 60 | 160 | (WC)Hans Schwaier [GER] d. (14)Cahill | 1-6 6-4 7-6 | | | | | | | | | |
25‑Apr‑1988 | Hamburg | Clay | R16 | 62 | 83 | Guillermo Vilas [ARG] d. Cahill | 6-3 4-6 6-1 | | | | | | | | | |
25‑Apr‑1988 | Hamburg | Clay | R32 | 62 | 13 | Cahill d. (3)Martin Jaite [ARG] | 2-6 7-6 6-1 | | | | | | | | | |
25‑Apr‑1988 | Hamburg | Clay | R64 | 62 | 74 | Cahill d. Nicklas Kroon [SWE] | 6-2 6-0 | | | | | | | | | |
18‑Apr‑1988 | Monte Carlo | Clay | R64 | 63 | 73 | Alberto Mancini [ARG] d. Cahill | 4-6 6-3 6-2 | | | | | | | | | |
11‑Apr‑1988 | Nice | Clay | R32 | 60 | 438 | (Q)Andreas Lesch [GER] d. Cahill | 6-3 7-5 | | | | | | | | | |
8‑Apr‑1988 | Davis Cup WG QF: FRA vs AUS | Clay | RR | 60 | 8 | Yannick Noah [FRA] d. Cahill | 3-6 6-4 6-4 6-2 | | | | | | | | | |
14‑Mar‑1988 | Key Biscayne | Hard | R64 | 66 | 20 | (19)Andrei Chesnokov [RUS] d. Cahill | 6-2 6-4 3-6 6-4 | | | | | | | | | |
14‑Mar‑1988 | Key Biscayne | Hard | R128 | 66 | 67 | Cahill d. Tim Wilkison [USA] | 7-5 6-4 6-7 6-3 | | | | | | | | | |
29‑Feb‑1988 | Indian Wells | Hard | R16 | 71 | 4 | (2)Miloslav Mecir [SVK] d. Cahill | 2-6 6-0 6-4 | | | | | | | | | |
29‑Feb‑1988 | Indian Wells | Hard | R32 | 71 | 49 | Cahill d. Aaron Krickstein [USA] | 6-4 6-4 | | | | | | | | | |
29‑Feb‑1988 | Indian Wells | Hard | R64 | 71 | 50 | Cahill d. Marian Vajda [SVK] | 2-6 6-0 6-4 | | | | | | | | | |
8‑Feb‑1988 | Rotterdam | Carpet | R32 | 67 | 98 | Libor Pimek [BEL] d. Cahill | 6-4 6-3 | | | | | | | | | |
11‑Jan‑1988 | Australian Open | Hard | R64 | 76 | 153 | Todd Witsken [USA] d. Cahill | 6-4 7-5 6-2 | | | | | | | | | |
11‑Jan‑1988 | Australian Open | Hard | R128 | 76 | 301 | Cahill d. (WC)Shane Barr [AUS] | 6-1 6-3 4-6 6-1 | | | | | | | | | |
4‑Jan‑1988 | Sydney Outdoor | Grass | QF | 83 | 40 | (3)Andrei Chesnokov [RUS] d. (6)Cahill | 6-3 7-5 | | | | | | | | | |
4‑Jan‑1988 | Sydney Outdoor | Grass | R16 | 83 | 175 | (6)Cahill d. Andrew Castle [GBR] | 7-6 6-3 | | | | | | | | | |
4‑Jan‑1988 | Sydney Outdoor | Grass | R32 | 83 | 212 | (6)Cahill d. (Q)Paul Chamberlin [USA] | 6-3 4-6 6-3 | | | | | | | | | |
28‑Dec‑1987 | Adelaide | Hard | R32 | 82 | 215 | Patrick Baur [GER] d. (6)Cahill | 6-7 7-5 6-2 | | | | | | | | | |