| 10. Round | 23/10/1999 | FC Groningen | - | Telstar | 5:0 | ||||
| 13. Round | 21/11/1999 | BV Emmen | - | FC Groningen | 2:1 | ||||
| 14. Round | 28/11/1999 | FC Groningen | - | Go Ahead Eagles | 6:1 |  |
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| 15. Round | 04/12/1999 | FC Groningen | - | Dordrecht '90 | 2:1 | ||||
| 17. Round | 18/12/1999 | FC Groningen | - | HFC Haarlem | 4:2 | ||||
| 18. Round | 24/01/2000 | FC Groningen | - | Helmond Sport | 2:0 | ||||
| 19. Round | 29/01/2000 | SBV Excelsior | - | FC Groningen | 1:0 | ||||
| 20. Round | 05/02/2000 | FC Groningen | - | RBC Roosendaal | 4:1 | ||||
| 23. Round | 28/02/2000 | FC Groningen | - | BV Veendam | 1:1 | ||||
| 24. Round | 06/03/2000 | ADO Den Haag | - | FC Groningen | 2:1 | ||||
| 25. Round | 11/03/2000 | VVV | - | FC Groningen | 1:0 | ||||
| 29. Round | 10/04/2000 | Heracles Almelo | - | FC Groningen | 1:0 | ||||
| 30. Round | 15/04/2000 | FC Groningen | - | BV Emmen | 2:0 | ||||
| 31. Round | 23/04/2000 | Go Ahead Eagles | - | FC Groningen | 2:3 | |
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| 32. Round | 01/05/2000 | Dordrecht '90 | - | FC Groningen | 1:3 | ||||
| 33. Round | 06/05/2000 | FC Groningen | - | FC Volendam | 3:0 | |
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| 34. Round | 13/05/2000 | HFC Haarlem | - | FC Groningen | 2:4 | |
Netherlands