11‑Dec‑1990 | Grand Slam Cup | Carpet | R16 | 21 | 5 | (4)Pete Sampras [USA] d. Cherkasov | 5-7 6-2 7-5 | | | | | | | | | |
5‑Nov‑1990 | Moscow | Carpet | F | 32 | 41 | (8)Cherkasov d. Tim Mayotte [USA] | 6-2 6-1 | | | | | | | | | |
5‑Nov‑1990 | Moscow | Carpet | SF | 32 | 105 | (8)Cherkasov d. Udo Riglewski [GER] | 6-1 7-6 | | | | | | | | | |
5‑Nov‑1990 | Moscow | Carpet | QF | 32 | 8 | (8)Cherkasov d. (2)Emilio Sanchez [ESP] | 6-3 6-3 | | | | | | | | | |
5‑Nov‑1990 | Moscow | Carpet | R16 | 32 | 71 | (8)Cherkasov d. Gilad Bloom [ISR] | 6-3 6-3 | | | | | | | | | |
5‑Nov‑1990 | Moscow | Carpet | R32 | 32 | 34 | (8)Cherkasov d. Amos Mansdorf [ISR] | 6-2 6-0 | | | | | | | | | |
29‑Oct‑1990 | Paris Masters | Carpet | R32 | 32 | 1 | (1)Stefan Edberg [SWE] d. Cherkasov | 6-2 6-3 | | | | | | | | | |
29‑Oct‑1990 | Paris Masters | Carpet | R64 | 32 | 60 | Cherkasov d. (WC)Fabrice Santoro [FRA] | 3-6 6-3 6-2 | | | | | | | | | |
22‑Oct‑1990 | Stockholm Masters | Carpet | R64 | 30 | 28 | Jakob Hlasek [SUI] d. Cherkasov | 6-3 6-4 | | | | | | | | | |
15‑Oct‑1990 | Lyon | Carpet | R32 | 28 | 70 | Mats Wilander [SWE] d. (5)Cherkasov | 6-2 3-6 6-3 | | | | | | | | | |
8‑Oct‑1990 | Tokyo Indoor | Carpet | QF | 31 | 2 | (2)Boris Becker [GER] d. (10)Cherkasov | 6-4 6-4 | | | | | | | | | |
8‑Oct‑1990 | Tokyo Indoor | Carpet | R16 | 31 | 88 | (10)Cherkasov d. Pat Cash [AUS] | 7-6 6-3 | | | | | | | | | |
8‑Oct‑1990 | Tokyo Indoor | Carpet | R32 | 31 | 229 | (10)Cherkasov d. (Q)Rick Leach [USA] | 6-1 6-4 | | | | | | | | | |
24‑Sep‑1990 | Basel | Hard | QF | 31 | 11 | (3)John Mcenroe [USA] d. Cherkasov | 6-3 7-5 | | | | | | | | | |
24‑Sep‑1990 | Basel | Hard | R16 | 31 | 18 | Cherkasov d. (5)Jim Courier [USA] | 3-6 6-2 6-3 | | | | | | | | | |
24‑Sep‑1990 | Basel | Hard | R32 | 31 | 81 | 6-4 6-1 | | | | | | | | | |
21‑Sep‑1990 | Davis Cup WG PO: URS vs ESP | Carpet | RR | 34 | 8 | Emilio Sanchez [ESP] d. Cherkasov | 6-3 6-7(7) 6-3 6-4 | | | | | | | | | |
21‑Sep‑1990 | Davis Cup WG PO: URS vs ESP | Carpet | RR | 34 | 37 | Cherkasov d. Sergi Bruguera [ESP] | 6-4 7-6(7) | | | | | | | | | |
27‑Aug‑1990 | US Open | Hard | QF | 50 | 4 | (4)Andre Agassi [USA] d. Cherkasov | 6-2 6-2 6-3 | | | | | | | | | |
27‑Aug‑1990 | US Open | Hard | R16 | 50 | 40 | Cherkasov d. Christo Van Rensburg [RSA] | 6-4 6-4 7-5 | | | | | | | | | |
27‑Aug‑1990 | US Open | Hard | R32 | 50 | 11 | Cherkasov d. (11)Michael Chang [USA] | 6-4 6-4 6-3 | | | | | | | | | |
27‑Aug‑1990 | US Open | Hard | R64 | 50 | 22 | Cherkasov d. Henri Leconte [FRA] | 1-6 6-1 6-4 6-3 | | | | | | | | | |
27‑Aug‑1990 | US Open | Hard | R128 | 50 | 280 | Cherkasov d. (WC)Robert Seguso [USA] | 6-0 6-7 6-2 6-3 | | | | | | | | | |
30‑Jul‑1990 | Kitzbuhel | Clay | QF | 54 | 7 | (3)Emilio Sanchez [ESP] d. (11)Cherkasov | 6-1 6-4 | | | | | | | | | |
30‑Jul‑1990 | Kitzbuhel | Clay | R16 | 54 | 25 | (11)Cherkasov d. (5)Marc Rosset [SUI] | 6-3 6-3 | | | | | | | | | |
30‑Jul‑1990 | Kitzbuhel | Clay | R32 | 54 | 137 | (11)Cherkasov d. Alexander Mronz [GER] | 6-2 6-4 | | | | | | | | | |
16‑Jul‑1990 | Stuttgart Outdoor | Clay | QF | 64 | 25 | (12)Henri Leconte [FRA] d. Cherkasov | 4-6 6-4 6-4 | | | | | | | | | |
16‑Jul‑1990 | Stuttgart Outdoor | Clay | R16 | 64 | 32 | Cherkasov d. Karel Novacek [CZE] | 7-5 3-6 6-4 | | | | | | | | | |
16‑Jul‑1990 | Stuttgart Outdoor | Clay | R32 | 64 | 26 | Cherkasov d. (13)Petr Korda [CZE] | 7-6 6-1 | | | | | | | | | |
16‑Jul‑1990 | Stuttgart Outdoor | Clay | R64 | 64 | 77 | 6-2 5-7 6-4 | | | | | | | | | |
9‑Jul‑1990 | Gstaad | Clay | R32 | 64 | 11 | (4)Andrei Chesnokov [RUS] d. Cherkasov | 6-3 7-6 | | | | | | | | | |
25‑Jun‑1990 | Wimbledon | Grass | R128 | 65 | 30 | Wally Masur [AUS] d. Cherkasov | 6-3 6-4 6-2 | | | | | | | | | |
18‑Jun‑1990 | Genova | Clay | R32 | 61 | 134 | Claudio Pistolesi [ITA] d. (6)Cherkasov | 6-0 7-6 | | | | | | | | | |
11‑Jun‑1990 | Florence | Clay | R32 | 59 | 70 | (6)Ronald Agenor [USA] d. Cherkasov | 7-6 7-6 | | | | | | | | | |
28‑May‑1990 | Roland Garros | Clay | R64 | 61 | 21 | (15)Guillermo Perez Roldan [ARG] d. Cherkasov | 7-5 6-4 6-3 | | | | | | | | | |
28‑May‑1990 | Roland Garros | Clay | R128 | 61 | 412 | Cherkasov d. (Q)Frederic Vitoux [FRA] | 6-0 6-4 6-4 | | | | | | | | | |
21‑May‑1990 | Dusseldorf | Clay | RR | 59 | 44 | Jordi Arrese [ESP] d. Cherkasov | 6-2 4-6 7-6 | | | | | | | | | |
21‑May‑1990 | Dusseldorf | Clay | RR | 59 | 4 | Brad Gilbert [USA] d. Cherkasov | 6-2 6-3 | | | | | | | | | |
21‑May‑1990 | Dusseldorf | Clay | RR | 59 | 3 | Boris Becker [GER] d. Cherkasov | 6-4 6-3 | | | | | | | | | |
14‑May‑1990 | Umag | Clay | SF | 74 | 53 | (2)Goran Ivanisevic [CRO] d. (5)Cherkasov | 6-3 5-7 6-4 | | | | | | | | | |
14‑May‑1990 | Umag | Clay | QF | 74 | 93 | (5)Cherkasov d. Eric Jelen [GER] | 6-2 6-0 | | | | | | | | | |
14‑May‑1990 | Umag | Clay | R16 | 74 | 148 | (5)Cherkasov d. Francisco Roig [ESP] | 6-3 6-4 | | | | | | | | | |
14‑May‑1990 | Umag | Clay | R32 | 74 | 257 | (5)Cherkasov d. (Q)Jose Clavet [ESP] | 6-2 6-4 | | | | | | | | | |
7‑May‑1990 | Hamburg Masters | Clay | R16 | 76 | 3 | (1)Boris Becker [GER] d. Cherkasov | 6-2 6-3 | | | | | | | | | |
7‑May‑1990 | Hamburg Masters | Clay | R32 | 76 | 74 | Cherkasov d. (WC)Jens Woehrmann [GER] | 6-4 6-1 | | | | | | | | | |
7‑May‑1990 | Hamburg Masters | Clay | R64 | 76 | 116 | Cherkasov d. (WC)Markus Zoecke [GER] | 6-2 6-2 | | | | | | | | | |
4‑May‑1990 | Davis Cup G1 SF: URS vs POR | Clay | RR | 72 | 165 | Nuno Marques [POR] d. Cherkasov | 6-7(4) 2-6 6-2 6-3 6-4 | | | | | | | | | |
4‑May‑1990 | Davis Cup G1 SF: URS vs POR | Clay | RR | 72 | 210 | Cherkasov d. Joao Cunha Silva [POR] | 6-2 6-2 | | | | | | | | | |
16‑Apr‑1990 | Nice | Clay | SF | 67 | 71 | (WC)Guy Forget [FRA] d. Cherkasov | 4-6 7-6 6-4 | | | | | | | | | |
16‑Apr‑1990 | Nice | Clay | QF | 67 | 7 | Cherkasov d. (1)Jay Berger [USA] | 2-6 6-2 6-3 | | | | | | | | | |
16‑Apr‑1990 | Nice | Clay | R16 | 67 | 60 | Cherkasov d. Michael Stich [GER] | 6-4 6-4 | | | | | | | | | |
16‑Apr‑1990 | Nice | Clay | R32 | 67 | 28 | Cherkasov d. (7)Petr Korda [CZE] | 0-6 7-5 7-5 | | | | | | | | | |
9‑Apr‑1990 | Barcelona | Clay | R32 | 68 | 164 | (WC)Carlos Costa [ESP] d. Cherkasov | 6-3 6-2 | | | | | | | | | |
9‑Apr‑1990 | Barcelona | Clay | R64 | 68 | 130 | Cherkasov d. (WC)Francisco Roig [ESP] | 6-3 6-3 | | | | | | | | | |
2‑Apr‑1990 | Estoril | Clay | R16 | 72 | 42 | Jordi Arrese [ESP] d. Cherkasov | 6-2 6-2 | | | | | | | | | |
2‑Apr‑1990 | Estoril | Clay | R32 | 72 | 28 | Cherkasov d. (7)Guillermo Perez Roldan [ARG] | 7-5 6-3 | | | | | | | | | |
16‑Mar‑1990 | Miami Masters | Hard | R128 | 70 | 101 | Cassio Motta [BRA] d. Cherkasov | 6-4 6-3 | | | | | | | | | |
26‑Feb‑1990 | Rotterdam | Carpet | R32 | 68 | 4 | (1)Brad Gilbert [USA] d. Cherkasov | 7-5 4-6 6-4 | | | | | | | | | |
12‑Feb‑1990 | Brussels | Carpet | R32 | 57 | 164 | (Q)Aki Rahunen [FIN] d. Cherkasov | 4-6 7-6 6-2 | | | | | | | | | |
5‑Feb‑1990 | Milan | Carpet | R32 | 56 | 6 | (2)John Mcenroe [USA] d. Cherkasov | 6-1 4-6 6-4 | | | | | | | | | |
15‑Jan‑1990 | Australian Open | Hard | QF | 89 | 1 | (1)Ivan Lendl [USA] d. Cherkasov | 6-3 6-2 6-3 | | | | | | | | | |
15‑Jan‑1990 | Australian Open | Hard | R16 | 89 | 18 | Cherkasov d. (9)Andres Gomez [ECU] | 2-6 6-3 7-6 7-6 | | | | | | | | | |
15‑Jan‑1990 | Australian Open | Hard | R32 | 89 | 57 | Cherkasov d. Jean Philippe Fleurian [FRA] | 6-4 6-4 7-5 | | | | | | | | | |
15‑Jan‑1990 | Australian Open | Hard | R64 | 89 | 75 | Cherkasov d. Glenn Layendecker [USA] | 6-4 5-7 7-5 6-0 | | | | | | | | | |
15‑Jan‑1990 | Australian Open | Hard | R128 | 89 | 336 | Cherkasov d. (Q)Shuzo Matsuoka [JPN] | 6-2 4-6 4-6 6-0 6-2 | | | | | | | | | |
8‑Jan‑1990 | Sydney Outdoor | Hard | R16 | 76 | 21 | (8)Yannick Noah [FRA] d. (Q)Cherkasov | 6-1 6-4 | | | | | | | | | |
8‑Jan‑1990 | Sydney Outdoor | Hard | R32 | 76 | 80 | (Q)Cherkasov d. Petr Korda [CZE] | 6-1 4-6 6-2 | | | | | | | | | |
1‑Jan‑1990 | Adelaide | Hard | R32 | 73 | 70 | (8)Marc Rosset [SUI] d. Cherkasov | 6-2 6-4 | | | | | | | | | |