| 1. Jornada | 14.08.1999 | RBC Roosendaal | - | BV Emmen | 1:3 |  |
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| 2. Jornada | 23.08.1999 | Go Ahead Eagles | - | RBC Roosendaal | 1:0 |  |
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| 4. Jornada | 05.09.1999 | FC Volendam | - | RBC Roosendaal | 2:1 | |
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| 5. Jornada | 11.09.1999 | RBC Roosendaal | - | HFC Haarlem | 2:1 | ||||
| 6. Jornada | 18.09.1999 | Helmond Sport | - | RBC Roosendaal | 0:2 | ||||
| 7. Jornada | 27.09.1999 | RBC Roosendaal | - | SBV Excelsior | 3:3 |  |
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| 8. Jornada | 02.10.1999 | Dordrecht '90 | - | RBC Roosendaal | 0:1 | ||||
| 9. Jornada | 18.10.1999 | SBV Eindhoven | - | RBC Roosendaal | 2:2 | ||||
| 10. Jornada | 23.10.1999 | RBC Roosendaal | - | FC Zwolle | 2:3 | |
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| 11. Jornada | 31.10.1999 | BV Veendam | - | RBC Roosendaal | 3:5 | ||||
| 13. Jornada | 20.11.1999 | VVV | - | RBC Roosendaal | 0:0 | ||||
| 18. Jornada | 22.01.2000 | BV Emmen | - | RBC Roosendaal | 2:1 |
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