 USA: US Open - Doubles - Main |
|---|
| 1/16-finals | Olsza A./Osterloh L. | Martinez C./Tarabini P. | 0:2 (1:6, 4:6) | details | 03.09.1999 |
| 1/32-finals | Olsza A./Osterloh L. | Nemeckova L./Zrubakova R. | 2:1 (7:6, 4:6, 6:2) | details | 01.09.1999 |
 United Kingdom: Wimbledon - Doubles - Main |
|---|
| 1/16-finals | Olsza A./Osterloh L. | Boogert K./Sidot A. | 0:2 (4:6, 3:6) | details | 01.07.1999 |
| 1/32-finals | Grande R./Saeki M. | Olsza A./Osterloh L. | 0:2 (4:6, 3:6) | details | 29.06.1999 |
 France: French Open - Doubles - Main |
|---|
| 1/16-finals | Olsza A./Osterloh L. | Farina Elia S./Habsudova K. | 0:2 (2:6, 1:6) | details | 30.05.1999 |
| 1/32-finals | Olsza A./Osterloh L. | Ellwood A./McShea L. | 2:1 (6:4, 66:7, 6:4) | details | 28.05.1999 |
| USA: Amelia Island - Main |
|---|
| 1/16-finals | Capriati J./Majoli I. | Olsza A./Osterloh L. | 2:1 (2:6, 6:4, 6:2) | details | 05.04.1999 |
| USA: Hilton Head - Doubles - Main |
|---|
| 1/8-finals | Olsza A./Osterloh L. | Likhovtseva E./Novotna J. | 0:2 (1:6, 1:6) | details | 31.03.1999 |
| 1/16-finals | Kunce K./Po K. | Olsza A./Osterloh L. | 0:2 (2:6, 4:6) | details | 29.03.1999 |
