| 1. Ronde | 14.08.1999 | Go Ahead Eagles | - | SBV Excelsior | 1:2 |  |
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| 2. Ronde | 23.08.1999 | Go Ahead Eagles | - | RBC Roosendaal | 1:0 | ||||
| 6. Ronde | 19.09.1999 | Go Ahead Eagles | - | ADO Den Haag | 0:2 | ||||
| 7. Ronde | 27.09.1999 | VVV | - | Go Ahead Eagles | 2:0 | ||||
| 8. Ronde | 02.10.1999 | Go Ahead Eagles | - | TOP Oss | 2:2 | ||||
| 9. Ronde | 16.10.1999 | Telstar | - | Go Ahead Eagles | 0:3 | ||||
| 10. Ronde | 23.10.1999 | Go Ahead Eagles | - | NAC Breda | 2:3 | |
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| 11. Ronde | 01.11.1999 | Heracles Almelo | - | Go Ahead Eagles | 1:0 | ||||
| 12. Ronde | 06.11.1999 | Go Ahead Eagles | - | BV Emmen | 1:3 | ||||
| 15. Ronde | 04.12.1999 | Go Ahead Eagles | - | FC Volendam | 4:1 | ||||
| 17. Ronde | 18.12.1999 | Go Ahead Eagles | - | Helmond Sport | 6:0 | ||||
| 16. Ronde | 22.12.1999 | HFC Haarlem | - | Go Ahead Eagles | 1:4 | |
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| 19. Ronde | 02.02.2000 | RBC Roosendaal | - | Go Ahead Eagles | 1:1 | |
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| 20. Ronde | 05.02.2000 | Go Ahead Eagles | - | SBV Eindhoven | 0:2 | ||||
| 21. Ronde | 14.02.2000 | FC Zwolle | - | Go Ahead Eagles | 1:1 | ||||
| 22. Ronde | 19.02.2000 | Go Ahead Eagles | - | BV Veendam | 1:2 | ||||
| 34. Ronde | 13.05.2000 | Helmond Sport | - | Go Ahead Eagles | 2:1 |
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