| 1996-10-07 | Vienna | Carpet | R16 | 25 |  Marc Rosset | 31 |  Andrei Medvedev | 7-6(5) 4-6 6-4 | H2H | 3 | 144 | 13 | 5 | 57.5% | 80.3% | 46.7% | 1/2 |
| 1996-10-07 | Vienna | Carpet | R32 | 31 | Andrei Medvedev | 57 |  Andrea Gaudenzi (LL) | 6-3 6-4 | H2H | 3 | 68 | 4 | 1 | 58.5% | 83.9% | 54.5% | 2/3 |
| 1996-09-30 | Lyon | Carpet | R32 | 23 |  Arnaud Boetsch | 29 | Andrei Medvedev | 6-2 6-4 | H2H | 3 | 71 | 3 | 2 | 53.7% | 79.3% | 64.0% | 0/0 |
| 1996-09-20 | Davis Cup G1 PO: UKR vs NOR | Clay | RR | 31 | Andrei Medvedev | 641 |  Jan Frode Andersen | 6-2 6-2 6-0 | H2H | 5 | - | - | - | - | - | - | - |
| 1996-09-20 | Davis Cup G1 PO: UKR vs NOR | Clay | RR | 31 | Andrei Medvedev | 61 | Christian Ruud | 6-2 6-1 | H2H | 3 | - | - | - | - | - | - | - |
| 1996-09-09 | Bournemouth | Clay | R32 | 512 |  Tom Kempers (Q) | 31 | Andrei Medvedev (4) | 6-7(5) 6-4 6-2 | H2H | 3 | 121 | 4 | 5 | 59.6% | 72.3% | 47.7% | 9/11 |
| 1996-08-26 | US Open | Hard | R16 | 6 |  Goran Ivanisevic (4) | 36 | Andrei Medvedev | 6-4 3-6 6-3 7-6(2) | H2H | 5 | - | 21 | 1 | 58.6% | 91.5% | 55.2% | 8/9 |
| 1996-08-26 | US Open | Hard | R32 | 36 | Andrei Medvedev | 42 |  Petr Korda | 6-2 6-4 6-3 | H2H | 5 | - | 4 | 3 | 65.2% | 81.0% | 41.9% | 3/4 |
| 1996-08-26 | US Open | Hard | R64 | 36 | Andrei Medvedev | 82 |  Jan Kroslak | 6-4 6-3 6-2 | H2H | 5 | 93 | 7 | 2 | 56.5% | 87.5% | 62.2% | 2/3 |
| 1996-08-26 | US Open | Hard | R128 | 36 | Andrei Medvedev | 100 | Jean-Philippe Fleurian | 6-2 6-0 6-1 | H2H | 5 | 77 | 3 | 3 | 49.3% | 91.2% | 42.9% | 2/3 |
