| 10. Round | 25/10/1999 | Helmond Sport | - | ADO Den Haag | 0:1 | ||||
| 11. Round | 31/10/1999 | VVV | - | Helmond Sport | 0:4 | ||||
| 12. Round | 06/11/1999 | Helmond Sport | - | TOP Oss | 0:0 | ||||
| 22. Round | 19/02/2000 | Helmond Sport | - | SBV Excelsior | 4:1 | ||||
| 27. Round | 25/03/2000 | ADO Den Haag | - | Helmond Sport | 1:0 | ||||
| 31. Round | 22/04/2000 | NAC Breda | - | Helmond Sport | 3:2 | ||||
| 32. Round | 01/05/2000 | Helmond Sport | - | Heracles Almelo | 1:1 |  |
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| 33. Round | 06/05/2000 | BV Emmen | - | Helmond Sport | 2:3 | ||||
| 34. Round | 13/05/2000 | Helmond Sport | - | Go Ahead Eagles | 2:1 |
Netherlands