 USA: Miami - Singles - Main |
|---|
| 1/32-finals | Enqvist T. | Courier J. | 2:1 (65:7, 6:3, 6:4) | details | 22.03.2000 |
| 1/64-finals | Courier J. | Nalbandian D. | 2:1 (6:3, 3:6, 7:5) | details | 20.03.2000 |
| USA: Indian Wells - Singles - Main |
|---|
| 1/32-finals | di P. A. | Courier J. | 2:1 (7:5, 4:6, 7:65) | details | 13.03.2000 |
| USA: Memphis - Singles - Main |
|---|
| 1/16-finals | Tieleman L. | Courier J. | 2:0 (7:62, 6:0) | details | 15.02.2000 |
| USA: San Jose - Singles - Main |
|---|
| Semi-finals | Courier J. | Philippoussis M. | 1:2 (6:4, 3:6, 4:6) | details | 12.02.2000 |
| Quarter-finals | Courier J. | Goldstein P. | 2:0 (6:4, 6:4) | details | 11.02.2000 |
| 1/8-finals | Courier J. | Gumy H. | 2:1 (7:5, 62:7, 7:64) | details | 09.02.2000 |
| 1/16-finals | Courier J. | Taino E. | 2:0 (6:3, 6:4) | details | 07.02.2000 |
 Australia: Australian Open - Singles - Main |
|---|
| 1/64-finals | Escude N. | Courier J. | 3:1 (64:7, 6:3, 7:5, 6:1) | details | 17.01.2000 |
 France: Paris - Singles - Main |
|---|
| Quarter-finals | Safin M. | Courier J. | 2:0 (6:2, 6:4) | details | 05.11.1999 |
| 1/8-finals | Courier J. | Enqvist T. | 2:1 (63:7, 7:64, 7:5) | details | 03.11.1999 |
| 1/16-finals | Moya C. | Courier J. | 0:2 (2:6, 1:6) | details | 02.11.1999 |
| 1/32-finals | di P. A. | Courier J. | 1:2 (65:7, 6:3, 66:7) | details | 01.11.1999 |
 Germany: Stuttgart 1 - Singles - Main |
|---|
| 1/16-finals | Courier J. | Corretja A. | 1:2 (3:6, 7:65, 3:6) | details | 26.10.1999 |
| 1/32-finals | Courier J. | Rosset M. | 2:1 (4:6, 7:66, 6:2) | details | 25.10.1999 |
| France: Lyon 2 - Singles - Main |
|---|
| 1/8-finals | Courier J. | Spadea V. | 0:2 (4:6, 4:6) | details | 20.10.1999 |
| 1/16-finals | Philippoussis M. | Courier J. | 1:2 (3:6, 6:3, 1:6) | details | 19.10.1999 |
| 1/32-finals | di P. A. | Courier J. | 1:2 (6:2, 62:7, 5:7) | details | 18.10.1999 |
| USA: US Open - Singles - Main |
|---|
| 1/64-finals | Dosedel S. | Courier J. | 3:0 (6:4, 6:4, 7:65) | details | 31.08.1999 |
| USA: Boston - Singles - Main |
|---|
| 1/16-finals | Courier J. | Sargsian S. | 0:2 (4:6, 4:6) | details | 23.08.1999 |
| USA: Cincinnati - Singles - Main |
|---|
| 1/16-finals | Courier J. | Pioline C. | 1:1 RET. (7:65, 64:7, 0:2) | details | 11.08.1999 |
| 1/32-finals | Ivanisevic G. | Courier J. | 0:2 (61:7, 2:6) | details | 09.08.1999 |
 Canada: Montreal - Singles - Main |
|---|
| Quarter-finals | Courier J. | Johansson T. | 0:2 (4:6, 4:6) | details | 06.08.1999 |
| 1/8-finals | Courier J. | Ferreira W. | 2:1 (63:7, 6:4, 7:5) | details | 05.08.1999 |
| 1/16-finals | Henman T. | Courier J. | 1:2 (1:6, 7:63, 4:6) | details | 04.08.1999 |
| 1/32-finals | Courier J. | Schuttler R. | 2:0 (7:62, 6:2) | details | 02.08.1999 |
 United Kingdom: Wimbledon - Singles - Main |
|---|
| 1/8-finals | Courier J. | Henman T. | 2:3 (6:4, 5:7, 5:7, 7:65, 7:9) | details | 06.07.1999 |
| 1/16-finals | Courier J. | Schalken S. | 3:2 (7:62, 3:6, 3:6, 7:5, 13:11) | details | 03.07.1999 |
| 1/32-finals | Moya C. | Courier J. | 2:3 (3:6, 6:3, 61:7, 6:3, 2:6) | details | 01.07.1999 |
| 1/64-finals | Cowan B. | Courier J. | 0:3 (3:6, 4:6, 4:6) | details | 29.06.1999 |
| United Kingdom: London - Singles - Main |
|---|
| 1/16-finals | Courier J. | Kucera K. | 1:2 (6:3, 4:6, 1:6) | details | 08.06.1999 |
| 1/32-finals | Carlsen K. | Courier J. | 1:2 (2:6, 6:4, 1:6) | details | 07.06.1999 |
| France: French Open - Singles - Main |
|---|
| 1/32-finals | Courier J. | Arazi H. | 1:3 (6:2, 3:6, 4:6, 1:6) | details | 27.05.1999 |
| 1/64-finals | Calatrava A. | Courier J. | 0:3 (1:6, 3:6, 5:7) | details | 24.05.1999 |
| USA: Delray Beach - Singles - Main |
|---|
| 1/16-finals | Courier J. | Mirnyi M. | 1:2 (6:4, 2:6, 66:7) | details | 03.05.1999 |
| USA: Verizon Tennis Challenge - Singles - Main |
|---|
| Semi-finals | Courier J. | Grosjean S. | 0:2 (63:7, 3:6) | details | 01.05.1999 |
| Quarter-finals | Rodriguez M. | Courier J. | 0:2 (1:6, 62:7) | details | 30.04.1999 |
| 1/8-finals | Courier J. | Gimelstob J. | 2:0 (6:1, 7:65) | details | 28.04.1999 |
| 1/16-finals | Courier J. | Tillstrom M. | 2:0 (6:3, 6:4) | details | 26.04.1999 |
| USA: Orlando - Singles - Main |
|---|
| Quarter-finals | Courier J. | Mirnyi M. | 1:2 (3:6, 63:7, 6:4) | details | 23.04.1999 |
| 1/8-finals | Courier J. | Blanco G. | 2:0 (7:5, 6:4) | details | 21.04.1999 |
