| 1. Round | 23/08/1998 | KRC Harelbeke | - | KV Kortrijk | 1:0 | ||||
| 7. Round | 20/09/1998 | KRC Harelbeke | - | KFC Germinal Ekeren | 0:4 | ||||
| 11. Round | 25/10/1998 | K.S.C. Eendracht Aalst | - | KRC Harelbeke | 2:2 | ||||
| 22. Round | 30/01/1999 | KVC Westerlo | - | KRC Harelbeke | 0:3 |  |
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| 23. Round | 14/02/1999 | KRC Harelbeke | - | Club Brugge KV | 0:2 | ||||
| 24. Round | 28/02/1999 | Germinal Beerschot | - | KRC Harelbeke | 0:2 | ||||
| 25. Round | 07/03/1999 | KRC Harelbeke | - | Sint-Truidense VV | 1:1 |  |
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| 26. Round | 13/03/1999 | Lommelse SK | - | KRC Harelbeke | 0:1 | ||||
| 27. Round | 21/03/1999 | KRC Harelbeke | - | RSC Anderlecht | 1:2 | |
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