| 2. Round | 19/09/1998 | Heracles Almelo | - | HFC Haarlem | 1:1 | ||||
| 3. Round | 10/10/1998 | BV Veendam | - | Heracles Almelo | 0:1 |  |
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| 3. Round | 19/10/1998 | Heracles Almelo | - | FC Zwolle | 0:5 | ||||
| 3. Round | 24/10/1998 | Dordrecht '90 | - | Heracles Almelo | 2:2 |  |
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| 4. Round | 02/11/1998 | Heracles Almelo | - | FC Groningen | 1:2 | ||||
| 4. Round | 07/11/1998 | VVV | - | Heracles Almelo | 3:0 | ||||
| 4. Round | 14/11/1998 | Helmond Sport | - | Heracles Almelo | 2:1 | ||||
| 5. Round | 02/12/1998 | Heracles Almelo | - | TOP Oss | 0:3 | ||||
| 5. Round | 16/12/1998 | FC Volendam | - | Heracles Almelo | 2:0 | ||||
| 5. Round | 21/12/1998 | Heracles Almelo | - | Go Ahead Eagles | 0:2 | ||||
| 7. Round | 20/02/1999 | HFC Haarlem | - | Heracles Almelo | 2:1 | ||||
| 8. Round | 20/03/1999 | FC Zwolle | - | Heracles Almelo | 0:1 | ||||
| 10. Round | 15/05/1999 | TOP Oss | - | Heracles Almelo | 0:0 | ||||
| 10. Round | 22/05/1999 | Heracles Almelo | - | FC Volendam | 2:0 |
Netherlands