| 6. Round | 30/01/1999 | Heracles Almelo | - | Telstar | 2:2 | ||||
| 7. Round | 20/02/1999 | HFC Haarlem | - | Heracles Almelo | 2:1 | ||||
| 7. Round | 24/02/1999 | ADO Den Haag | - | Heracles Almelo | 0:2 | ||||
| 7. Round | 27/02/1999 | Heracles Almelo | - | BV Veendam | 2:1 |  |
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| 8. Round | 03/03/1999 | Heracles Almelo | - | RBC Roosendaal | 0:1 | ||||
| 8. Round | 06/03/1999 | FC Den Bosch | - | Heracles Almelo | 1:2 | |
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| 8. Round | 13/03/1999 | Heracles Almelo | - | SBV Eindhoven | 2:1 | ||||
| 8. Round | 20/03/1999 | FC Zwolle | - | Heracles Almelo | 0:1 | ||||
| 9. Round | 03/04/1999 | Heracles Almelo | - | Dordrecht '90 | 1:0 |  |
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| 9. Round | 12/04/1999 | FC Groningen | - | Heracles Almelo | 2:1 | ||||
| 9. Round | 19/04/1999 | Heracles Almelo | - | VVV | 4:2 | ||||
| 9. Round | 24/04/1999 | Telstar | - | Heracles Almelo | 2:2 | ||||
| 10. Round | 01/05/1999 | Heracles Almelo | - | Helmond Sport | 0:1 | ||||
| 10. Round | 10/05/1999 | Heracles Almelo | - | BV Emmen | 0:0 | ||||
| 10. Round | 15/05/1999 | TOP Oss | - | Heracles Almelo | 0:0 | ||||
| 10. Round | 22/05/1999 | Heracles Almelo | - | FC Volendam | 2:0 |
Netherlands