| 1. Round | 30/07/1999 | LB Châteauroux | - | ASOA Valence | 3:3 | ||||
| 3. Round | 12/08/1999 | LB Châteauroux | - | FC Gueugnon | 0:1 | ||||
| 4. Round | 16/08/1999 | FC Sochaux | - | LB Châteauroux | 1:2 | ||||
| 5. Round | 20/08/1999 | LB Châteauroux | - | Lille OSC | 2:3 |  |
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| 23. Round | 14/01/2000 | Lille OSC | - | LB Châteauroux | 1:0 | ||||
| 24. Round | 25/01/2000 | LB Châteauroux | - | Amiens SC | 0:0 | ||||
| 25. Round | 01/02/2000 | EA Guingamp | - | LB Châteauroux | 3:2 | |
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| 26. Round | 04/02/2000 | LB Châteauroux | - | Stade Lavallois | 3:1 | |
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| 28. Round | 25/02/2000 | LB Châteauroux | - | OGC Nice | 3:0 | ||||
| 29. Round | 10/03/2000 | AC Ajaccio | - | LB Châteauroux | 1:0 | ||||
| 30. Round | 23/03/2000 | US Créteil-Lusitanos | - | LB Châteauroux | 0:1 | ||||
| 31. Round | 30/03/2000 | LB Châteauroux | - | Louhans-Cuiseaux | 3:2 | ||||
| 32. Round | 07/04/2000 | Toulouse FC | - | LB Châteauroux | 0:1 | ||||
| 33. Round | 14/04/2000 | LB Châteauroux | - | ES Wasquehal | 1:1 | ||||
| 34. Round | 20/04/2000 | Chamois Niortais | - | LB Châteauroux | 1:0 | ||||
| 35. Round | 28/04/2000 | LB Châteauroux | - | Le Mans UC 72 | 3:2 |  |
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| 38. Round | 19/05/2000 | ASOA Valence | - | LB Châteauroux | 2:2 |
Martinique