| 3. Round | 03/10/1998 | BV Veendam | - | TOP Oss | 0:1 |  |
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| 3. Round | 18/10/1998 | TOP Oss | - | FC Den Bosch | 0:2 | ||||
| 3. Round | 26/10/1998 | SBV Eindhoven | - | TOP Oss | 1:2 | ||||
| 3. Round | 31/10/1998 | TOP Oss | - | FC Zwolle | 1:1 | ||||
| 9. Round | 10/04/1999 | FC Zwolle | - | TOP Oss | 1:0 | ||||
| 9. Round | 17/04/1999 | TOP Oss | - | Dordrecht '90 | 2:2 | ||||
| 9. Round | 24/04/1999 | FC Groningen | - | TOP Oss | 1:1 | ||||
| 10. Round | 01/05/1999 | TOP Oss | - | VVV | 5:0 | ||||
| 10. Round | 08/05/1999 | Telstar | - | TOP Oss | 2:2 | |
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| 10. Round | 15/05/1999 | TOP Oss | - | Heracles Almelo | 0:0 | ||||
| 10. Round | 22/05/1999 | BV Emmen | - | TOP Oss | 2:1 |
Netherlands