| 1. Round | 13/08/1999 | Helmond Sport | - | FC Groningen | 2:3 | ||||
| 6. Round | 18/09/1999 | Helmond Sport | - | RBC Roosendaal | 0:2 |  |
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| 7. Round | 27/09/1999 | SBV Eindhoven | - | Helmond Sport | 2:1 | ||||
| 13. Round | 20/11/1999 | Telstar | - | Helmond Sport | 1:0 | ||||
| 14. Round | 27/11/1999 | Helmond Sport | - | NAC Breda | 0:3 | |
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| 15. Round | 04/12/1999 | Heracles Almelo | - | Helmond Sport | 2:3 | ||||
| 16. Round | 11/12/1999 | Helmond Sport | - | BV Emmen | 3:2 | ||||
| 17. Round | 18/12/1999 | Go Ahead Eagles | - | Helmond Sport | 6:0 |
Netherlands