| 1. Round | 30/08/1998 | FC Volendam | - | TOP Oss | 3:2 | ||||
| 3. Round | 18/10/1998 | TOP Oss | - | FC Den Bosch | 0:2 |  |
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| 3. Round | 26/10/1998 | SBV Eindhoven | - | TOP Oss | 1:2 | ||||
| 4. Round | 07/11/1998 | Dordrecht '90 | - | TOP Oss | 3:3 | |
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| 4. Round | 14/11/1998 | VVV | - | TOP Oss | 2:3 | ||||
| 8. Round | 13/03/1999 | TOP Oss | - | BV Veendam | 2:0 | ||||
| 8. Round | 21/03/1999 | FC Den Bosch | - | TOP Oss | 2:1 | ||||
| 9. Round | 03/04/1999 | TOP Oss | - | SBV Eindhoven | 0:4 |
Netherlands