USA: US Open - Doubles - Main |
| 1/32-finals | Olhovskiy A./Prinosil D. | Boutter J./Santoro F. | 0:2 (2:6, 2:6) | details | 30.08.2000 |
USA: Washington - Doubles - Main |
| 1/16-finals | Olhovskiy A./Prinosil D. | Shimada T./Wakefield M. | 0:2 (3:6, 4:6) | details | 14.08.2000 |
Russia: Moscow - Doubles - Main |
| Quarter-finals | Damm M./Mirnyi M. | Olhovskiy A./Prinosil D. | 2:1 (611:7, 6:3, 6:4) | details | 10.11.1999 |
| 1/8-finals | Kafelnikov Y./Tarango J. | Olhovskiy A./Prinosil D. | 1:2 (67:7, 6:3, 4:6) | details | 08.11.1999 |
Germany: Stuttgart 1 - Doubles - Main |
| Semi-finals | Olhovskiy A./Prinosil D. | Black B./Bjorkman J. | 1:2 (6:2, 4:6, 65:7) | details | 30.10.1999 |
| Quarter-finals | Lareau S./O'Brien A. | Olhovskiy A./Prinosil D. | 1:2 (3:6, 6:4, 3:6) | details | 28.10.1999 |
| 1/8-finals | Novak J./Rikl D. | Olhovskiy A./Prinosil D. | 1:2 (6:1, 2:6, 4:6) | details | 26.10.1999 |
Switzerland: Basel - Doubles - Main |
| Semi-finals | Olhovskiy A./Prinosil D. | Novak J./Rikl D. | 0:2 (2:6, 64:7) | details | 08.10.1999 |
| Quarter-finals | Damm M./Koenig R. | Olhovskiy A./Prinosil D. | 0:2 (2:6, 3:6) | details | 06.10.1999 |
| 1/8-finals | Olhovskiy A./Prinosil D. | Johnson D./Suk C. | 2:0 (7:64, 6:2) | details | 04.10.1999 |
USA: US Open - Doubles - Main |
| Semi-finals | Bhupathi M./Paes L. | Olhovskiy A./Prinosil D. | 2:0 (6:4, 6:3) | details | 09.09.1999 |
| Quarter-finals | Olhovskiy A./Prinosil D. | Black W./Stolle S. | 2:0 (6:4, 6:2) | details | 07.09.1999 |
| 1/8-finals | Olhovskiy A./Prinosil D. | MacPhie B./Zimonjic N. | 2:0 (7:63, 6:3) | details | 05.09.1999 |
| 1/16-finals | Adams D./De Jager J. | Olhovskiy A./Prinosil D. | 0:2 (4:6, 66:7) | details | 03.09.1999 |
USA: Indianapolis - Doubles - Main |
| 1/8-finals | Olhovskiy A./Prinosil D. | Knowles M./Nestor D. | 1:2 (6:2, 1:6, 3:6) | details | 18.08.1999 |
| 1/16-finals | Enqvist T./Johansson T. | Olhovskiy A./Prinosil D. | 0:2 (3:6, 2:6) | details | 16.08.1999 |
France: French Open - Doubles - Main |
| 1/16-finals | Eltingh J./Haarhuis P. | Olhovskiy A./Prinosil D. | 2:0 (6:2, 6:3) | details | 31.05.1998 |
| 1/32-finals | Ivanisevic G./Philippoussis M. | Olhovskiy A./Prinosil D. | 1:2 (6:3, 62:7, 2:6) | details | 29.05.1998 |