| 4. Round | 29/08/1999 | KRC Harelbeke | - | Lierse SK (old) | 0:3 | ||||
| 5. Round | 11/09/1999 | Lommelse SK | - | KRC Harelbeke | 0:2 | ||||
| 7. Round | 25/09/1999 | Sint-Truidense VV | - | KRC Harelbeke | 2:0 | ||||
| 8. Round | 03/10/1999 | KRC Harelbeke | - | Sporting Lokeren | 2:3 | ||||
| 9. Round | 13/10/1999 | Germinal Beerschot | - | KRC Harelbeke | 1:0 | ||||
| 13. Round | 10/11/1999 | KRC Harelbeke | - | KV Mechelen | 5:2 | ||||
| 18. Round | 12/01/2000 | KRC Harelbeke | - | RSC Charleroi | 4:1 | ||||
| 20. Round | 23/01/2000 | KRC Harelbeke | - | KSK Beveren | 0:5 | ||||
| 24. Round | 20/02/2000 | KRC Harelbeke | - | Sint-Truidense VV | 3:2 | ||||
| 26. Round | 12/03/2000 | KRC Harelbeke | - | Germinal Beerschot | 1:0 | ||||
| 32. Round | 22/04/2000 | KAA Gent | - | KRC Harelbeke | 4:2 |
France