| 3. Jornada | 28.08.1999 | VVV | - | Telstar | 1:0 | ||||
| 4. Jornada | 05.09.1999 | Telstar | - | TOP Oss | 3:0 | ||||
| 5. Jornada | 11.09.1999 | Telstar | - | Dordrecht '90 | 0:3 | ||||
| 2. Jornada | 15.09.1999 | Telstar | - | ADO Den Haag | 2:0 | ||||
| 6. Jornada | 18.09.1999 | NAC Breda | - | Telstar | 2:0 | ||||
| 7. Jornada | 27.09.1999 | Telstar | - | Heracles Almelo | 0:2 | ||||
| 8. Jornada | 02.10.1999 | BV Emmen | - | Telstar | 2:0 | ||||
| 9. Jornada | 16.10.1999 | Telstar | - | Go Ahead Eagles | 0:3 | ||||
| 15. Jornada | 04.12.1999 | Telstar | - | RBC Roosendaal | 2:4 | ||||
| 16. Jornada | 11.12.1999 | SBV Eindhoven | - | Telstar | 3:0 | ||||
| 17. Jornada | 18.12.1999 | Telstar | - | FC Zwolle | 0:4 |  |
Países Bajos