World: World Tour Finals - Hartford - Doubles - Play Offs |
| Semi-finals | Lareau S./O'Brien A. | Black W./Stolle S. | 2:0 (6:3, 7:5) | details | 19.11.1999 |
World: World Tour Finals - Hartford - Doubles - Main |
| Group A | Black W./Stolle S. | Bhupathi M./Paes L. | 2:1 (65:7, 7:5, 6:2) | details | 18.11.1999 |
| Group A | Black W./Stolle S. | Norval P./Ullyett K. | 2:0 (7:65, 6:1) | details | 17.11.1999 |
| Group A | Ferreira E./Leach R. | Black W./Stolle S. | 2:0 (6:3, 6:2) | details | 16.11.1999 |
Sweden: Stockholm - Doubles - Main |
| Semi-finals | Norval P./Ullyett K. | Black W./Stolle S. | 2:1 (3:6, 7:63, 6:4) | details | 13.11.1999 |
| Quarter-finals | Bhupathi M./Tramacchi P. | Black W./Stolle S. | 0:2 (1:6, 3:6) | details | 10.11.1999 |
| 1/8-finals | Federer R./Norman M. | Black W./Stolle S. | 0:2 (3:6, 0:6) | details | 08.11.1999 |
France: Paris - Doubles - Main |
| 1/8-finals | Knowles M./Nestor D. | Black W./Stolle S. | 2:1 (4:6, 7:63, 6:3) | details | 03.11.1999 |
USA: US Open - Doubles - Main |
| Quarter-finals | Olhovskiy A./Prinosil D. | Black W./Stolle S. | 2:0 (6:4, 6:2) | details | 07.09.1999 |
| 1/8-finals | Johnson D./Suk C. | Black W./Stolle S. | 0:2 (3:6, 4:6) | details | 05.09.1999 |
| 1/16-finals | Albano P./Carbonell T. | Black W./Stolle S. | 0:2 (3:6, 4:6) | details | 03.09.1999 |
| 1/32-finals | Del Rio D./Rodriguez M. | Black W./Stolle S. | 0:2 (1:6, 4:6) | details | 01.09.1999 |
USA: Washington - Doubles - Main |
| Quarter-finals | Black W./Stolle S. | Norval P./Ullyett K. | 0:2 (4:6, 4:6) | details | 19.08.1999 |
| 1/8-finals | Black W./Stolle S. | Arnold-Ker L./Ran E. | 2:0 (6:3, 6:3) | details | 18.08.1999 |
USA: Cincinnati - Doubles - Main |
| Quarter-finals | Black W./Stolle S. | Black B./Bjorkman J. | 0:2 (3:6, 67:7) | details | 13.08.1999 |
| 1/8-finals | Black W./Stolle S. | Lareau S./O'Brien A. | 2:1 (3:6, 6:1, 6:4) | details | 11.08.1999 |
Canada: Montreal - Doubles - Main |
| 1/8-finals | Grabb J./Ivanisevic G. | Black W./Stolle S. | 2:0 (6:4, 6:4) | details | 04.08.1999 |
USA: Los Angeles - Doubles - Main |
| Semi-finals | Black B./Ferreira W. | Black W./Stolle S. | 2:0 (6:4, 6:2) | details | 30.07.1999 |
| Quarter-finals | Hewitt L./Woodforde M. | Black W./Stolle S. | 1:2 (6:3, 3:6, 2:6) | details | 28.07.1999 |
| 1/8-finals | Joyce M./Spencer K. | Black W./Stolle S. | 0:2 (2:6, 1:6) | details | 26.07.1999 |
United Kingdom: Wimbledon - Doubles - Main |
| Quarter-finals | Black W./Stolle S. | Delaitre O./Santoro F. | 1:3 (7:5, 4:6, 2:6, 5:7) | details | 03.07.1999 |
| 1/8-finals | Black W./Stolle S. | Cowan B./Whitehouse W. | 3:0 (6:4, 7:63, 6:3) | details | 01.07.1999 |
| 1/16-finals | Black W./Stolle S. | Navarra M./Pescosolido S. | 3:0 (7:5, 6:3, 6:3) | details | 30.06.1999 |
| 1/32-finals | Black W./Stolle S. | Humphries S./Waite J. | 3:1 (6:4, 6:4, 66:7, 6:1) | details | 28.06.1999 |
United Kingdom: London - Doubles - Main |
| 1/8-finals | Humphries S./Waite J. | Black W./Stolle S. | 2:1 (4:6, 6:3, 6:4) | details | 08.06.1999 |
France: French Open - Doubles - Main |
| 1/8-finals | Prinosil D./Vacek D. | Black W./Stolle S. | 2:1 (3:6, 7:5, 13:11) | details | 29.05.1999 |
| 1/16-finals | Merklein M./Sell M. | Black W./Stolle S. | 0:2 (3:6, 62:7) | details | 27.05.1999 |
| 1/32-finals | Martin A./Rosner P. | Black W./Stolle S. | 0:2 (3:6, 1:6) | details | 25.05.1999 |
Italy: Rome - Doubles - Main |
| 1/16-finals | Brandi C./Bertolini M. | Black W./Stolle S. | 2:0 (6:3, 6:1) | details | 10.05.1999 |
USA: Miami - Doubles - Main |
| Final | Becker B./Gambill J. | Black W./Stolle S. | 0:2 (1:6, 1:6) | details | 28.03.1999 |
| Semi-finals | Kulti N./Tillstrom M. | Black W./Stolle S. | 1:2 (7:6, 6:7, 3:6) | details | 27.03.1999 |
| Quarter-finals | Black W./Stolle S. | Florent A./MacPherson D. | 2:1 (6:3, 6:7, 6:4) | details | 23.03.1999 |
| 1/8-finals | Black W./Stolle S. | Flach D./Tarango J. | 2:0 (6:3, 6:4) | details | 20.03.1999 |
| 1/16-finals | Black W./Stolle S. | Roig F./Sanchez J. | 2:0 (6:1, 7:5) | details | 17.03.1999 |
USA: Indian Wells - Doubles - Main |
| Final | Ferreira E./Leach R. | Black W./Stolle S. | 0:2 (64:7, 3:6) | details | 14.03.1999 |
| Semi-finals | Florent A./MacPherson D. | Black W./Stolle S. | 0:2 (6:7, 4:6) | details | 13.03.1999 |
| Quarter-finals | Black W./Stolle S. | Bryan B./Bryan M. | 2:0 (6:4, 7:5) | details | 10.03.1999 |
| 1/8-finals | Black W./Stolle S. | Haggard C./Tramacchi P. | 2:0 (6:4, 6:3) | details | 09.03.1999 |
| 1/16-finals | Adams D./De Jager J. | Black W./Stolle S. | 1:2 (2:6, 6:3, 2:6) | details | 08.03.1999 |
Italy: London - Doubles - Main |
| 1/8-finals | Black W./Stolle S. | Eagle J./Florent A. | 1:2 (7:6, 2:6, 6:7) | details | 22.02.1999 |
Netherlands: Rotterdam - Doubles - Main |
| 1/8-finals | Adams D./De Jager J. | Black W./Stolle S. | 2:0 (6:3, 6:1) | details | 15.02.1999 |
United Arab Emirates: Dubai - Doubles - Main |
| Final | Black W./Stolle S. | Adams D./De Jager J. | 2:1 (4:6, 6:1, 6:4) | details | 14.02.1999 |
| Semi-finals | Eagle J./Florent A. | Black W./Stolle S. | 1:2 (4:6, 6:3, 3:6) | details | 12.02.1999 |
| Quarter-finals | Norval P./Ullyett K. | Black W./Stolle S. | 0:2 (2:6, 2:6) | details | 10.02.1999 |
| 1/8-finals | Carbonell T./Haggard C. | Black W./Stolle S. | 1:2 (4:6, 6:2, 3:6) | details | 08.02.1999 |
Australia: Australian Open - Doubles - Main |
| 1/8-finals | Black W./Stolle S. | Woodbridge T./Woodforde M. | 0:2 (5:7, 0:6) | details | 25.01.1999 |
| 1/16-finals | Black W./Stolle S. | Haggard C./Nyborg P. | 2:0 (6:3, 6:3) | details | 20.01.1999 |
| 1/32-finals | Black W./Stolle S. | Mitchell T./Painter A. | 2:0 (7:65, 7:63) | details | 18.01.1999 |
Australia: Sydney - Doubles - Main |
| Quarter-finals | Black W./Stolle S. | Kratzmann A./Tramacchi P. | 1:2 (6:4, 3:6, 4:6) | details | 13.01.1999 |
| 1/8-finals | Black W./Stolle S. | Adams D./De Jager J. | 2:1 (3:6, 6:4, 6:4) | details | 11.01.1999 |