| 2. Round | 10/09/1999 | Heracles Almelo | - | FC Zwolle | 1:1 | ||||
| 5. Round | 13/09/1999 | VVV | - | Heracles Almelo | 0:1 | ||||
| 6. Round | 18/09/1999 | Heracles Almelo | - | TOP Oss | 2:0 | ||||
| 7. Round | 27/09/1999 | Telstar | - | Heracles Almelo | 0:2 | ||||
| 8. Round | 04/10/1999 | Heracles Almelo | - | NAC Breda | 4:3 |  |
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| 9. Round | 18/10/1999 | Heracles Almelo | - | Dordrecht '90 | 1:1 | ||||
| 11. Round | 01/11/1999 | Heracles Almelo | - | Go Ahead Eagles | 1:0 | |
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| 12. Round | 06/11/1999 | FC Groningen | - | Heracles Almelo | 1:0 | ||||
| 31. Round | 22/04/2000 | Heracles Almelo | - | HFC Haarlem | 2:0 | ||||
| 32. Round | 01/05/2000 | Helmond Sport | - | Heracles Almelo | 1:1 |
Netherlands