| 3. Round | 18/10/1998 | TOP Oss | - | FC Den Bosch | 0:2 | ||||
| 3. Round | 24/10/1998 | FC Den Bosch | - | FC Volendam | 3:1 | ||||
| 4. Round | 01/11/1998 | SBV Excelsior | - | FC Den Bosch | 1:1 | ||||
| 4. Round | 07/11/1998 | FC Den Bosch | - | Go Ahead Eagles | 5:2 |  |
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| 4. Round | 12/11/1998 | FC Den Bosch | - | Telstar | 0:0 | ||||
| 4. Round | 14/11/1998 | FC Den Bosch | - | RBC Roosendaal | 4:1 | ||||
| 4. Round | 22/11/1998 | HFC Haarlem | - | FC Den Bosch | 1:7 | ||||
| 4. Round | 28/11/1998 | FC Den Bosch | - | BV Veendam | 2:1 | ||||
| 7. Round | 20/02/1999 | FC Den Bosch | - | VVV | 3:0 | ||||
| 7. Round | 27/02/1999 | Telstar | - | FC Den Bosch | 0:1 | ||||
| 8. Round | 06/03/1999 | FC Den Bosch | - | Heracles Almelo | 1:2 | ||||
| 8. Round | 21/03/1999 | FC Den Bosch | - | TOP Oss | 2:1 | ||||
| 8. Round | 28/03/1999 | FC Volendam | - | FC Den Bosch | 1:4 | ||||
| 9. Round | 25/04/1999 | FC Den Bosch | - | ADO Den Haag | 4:1 | |
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| 10. Round | 02/05/1999 | RBC Roosendaal | - | FC Den Bosch | 1:2 | ||||
| 10. Round | 08/05/1999 | FC Den Bosch | - | HFC Haarlem | 2:2 | ||||
| 10. Round | 22/05/1999 | FC Den Bosch | - | Helmond Sport | 4:4 |
Netherlands