| 1. Round | 22/08/1998 | BV Emmen | - | FC Volendam | 4:0 | ||||
| 1. Round | 30/08/1998 | FC Volendam | - | TOP Oss | 3:2 | ||||
| 2. Round | 09/09/1998 | FC Volendam | - | Helmond Sport | 4:2 | ||||
| 2. Round | 12/09/1998 | SBV Excelsior | - | FC Volendam | 3:1 |  |
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| 3. Round | 17/10/1998 | FC Volendam | - | BV Veendam | 3:1 | ||||
| 3. Round | 24/10/1998 | FC Den Bosch | - | FC Volendam | 3:1 | ||||
| 4. Round | 07/11/1998 | FC Zwolle | - | FC Volendam | 2:2 | ||||
| 4. Round | 16/11/1998 | FC Groningen | - | FC Volendam | 3:2 | ||||
| 4. Round | 22/11/1998 | FC Volendam | - | VVV | 0:2 | ||||
| 4. Round | 28/11/1998 | Telstar | - | FC Volendam | 4:2 | ||||
| 5. Round | 13/12/1998 | FC Volendam | - | BV Emmen | 3:1 | ||||
| 5. Round | 16/12/1998 | FC Volendam | - | Heracles Almelo | 2:0 | ||||
| 5. Round | 19/12/1998 | TOP Oss | - | FC Volendam | 1:2 | ||||
| 6. Round | 03/02/1999 | FC Volendam | - | Dordrecht '90 | 4:1 | ||||
| 7. Round | 07/02/1999 | FC Volendam | - | ADO Den Haag | 1:1 | ||||
| 7. Round | 20/02/1999 | Go Ahead Eagles | - | FC Volendam | 0:0 | ||||
| 7. Round | 24/02/1999 | Helmond Sport | - | FC Volendam | 0:1 |
Netherlands