| 1. Round | 22/08/1998 | TOP Oss | - | Helmond Sport | 2:1 |  |
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| 1. Round | 30/08/1998 | FC Volendam | - | TOP Oss | 3:2 |  |
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| 2. Round | 05/09/1998 | TOP Oss | - | SBV Excelsior | 3:0 | ||||
| 2. Round | 12/09/1998 | Go Ahead Eagles | - | TOP Oss | 3:0 | ||||
| 2. Round | 20/09/1998 | TOP Oss | - | ADO Den Haag | 0:1 | ||||
| 3. Round | 31/10/1998 | TOP Oss | - | FC Zwolle | 1:1 | ||||
| 4. Round | 07/11/1998 | Dordrecht '90 | - | TOP Oss | 3:3 | ||||
| 4. Round | 14/11/1998 | VVV | - | TOP Oss | 2:3 | ||||
| 5. Round | 02/12/1998 | Heracles Almelo | - | TOP Oss | 0:3 | ||||
| 5. Round | 05/12/1998 | TOP Oss | - | BV Emmen | 0:1 | ||||
| 5. Round | 12/12/1998 | Helmond Sport | - | TOP Oss | 2:0 | ||||
| 5. Round | 19/12/1998 | TOP Oss | - | FC Volendam | 1:2 | |
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| 7. Round | 06/02/1999 | SBV Excelsior | - | TOP Oss | 3:0 | ||||
| 7. Round | 20/02/1999 | ADO Den Haag | - | TOP Oss | 1:1 | ||||
| 7. Round | 27/02/1999 | TOP Oss | - | RBC Roosendaal | 0:3 | ||||
| 10. Round | 01/05/1999 | TOP Oss | - | VVV | 5:0 | |
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| 10. Round | 08/05/1999 | Telstar | - | TOP Oss | 2:2 | ||||
| 10. Round | 15/05/1999 | TOP Oss | - | Heracles Almelo | 0:0 | ||||
| 10. Round | 22/05/1999 | BV Emmen | - | TOP Oss | 2:1 |
Netherlands