18‑Oct‑1988 | Tokyo Indoor | Carpet | R32 | 83 | 62 | Eric Jelen [GER] d. Olhovskiy | 6-3 6-2 | | | | | | | | | |
22‑Aug‑1988 | Rye Brook | Hard | R16 | 74 | 91 | Tim Wilkison [USA] d. (6)Olhovskiy | 6-1 6-0 | | | | | | | | | |
22‑Aug‑1988 | Rye Brook | Hard | R32 | 74 | 149 | (6)Olhovskiy d. (WC)John Ross [USA] | 7-6 6-4 | | | | | | | | | |
15‑Aug‑1988 | Cincinnati | Hard | R64 | 72 | 173 | Gary Muller [RSA] d. (WC)Olhovskiy | 6-4 7-5 | | | | | | | | | |
8‑Aug‑1988 | Prague | Clay | R16 | 79 | 137 | Karel Novacek [CZE] d. (8)Olhovskiy | 6-1 7-6 | | | | | | | | | |
8‑Aug‑1988 | Prague | Clay | R32 | 79 | 262 | (8)Olhovskiy d. Michele Fioroni [ITA] | 6-4 6-2 | | | | | | | | | |
20‑Jun‑1988 | Wimbledon | Grass | R16 | 151 | 4 | (4)Pat Cash [AUS] d. (Q)Olhovskiy | 6-3 6-3 6-3 | | | | | | | | | |
20‑Jun‑1988 | Wimbledon | Grass | R32 | 151 | 93 | (Q)Olhovskiy d. Chris Pridham [CAN] | 3-6 6-3 6-4 6-3 | | | | | | | | | |
20‑Jun‑1988 | Wimbledon | Grass | R64 | 151 | 143 | (Q)Olhovskiy d. Pieter Aldrich [RSA] | 6-4 6-4 6-2 | | | | | | | | | |
20‑Jun‑1988 | Wimbledon | Grass | R128 | 151 | 40 | (Q)Olhovskiy d. Tomas Smid [CZE] | 6-4 6-4 6-4 | | | | | | | | | |
11‑Jan‑1988 | Australian Open | Hard | R128 | 207 | 156 | Rick Leach [USA] d. Olhovskiy | 6-3 6-2 6-4 | | | | | | | | | |
4‑Jan‑1988 | Sydney Outdoor | Grass | R16 | 232 | 100 | (7)Joey Rive [USA] d. (Q)Olhovskiy | 6-2 6-7 7-6 | | | | | | | | | |
4‑Jan‑1988 | Sydney Outdoor | Grass | R32 | 232 | 203 | (Q)Olhovskiy d. Huub Van Boeckel [NED] | 6-2 7-5 | | | | | | | | | |
28‑Dec‑1987 | Wellington | Hard | R32 | 232 | 120 | Broderick Dyke [AUS] d. Olhovskiy | 6-1 6-4 | | | | | | | | | |