| 7. Jornada | 27.02.1999 | Dordrecht '90 | - | Helmond Sport | 0:2 |  |
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| 8. Jornada | 08.03.1999 | Helmond Sport | - | Go Ahead Eagles | 2:2 | |
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| 8. Jornada | 13.03.1999 | FC Groningen | - | Helmond Sport | 2:0 | ||||
| 8. Jornada | 17.03.1999 | Helmond Sport | - | ADO Den Haag | 1:1 | ||||
| 9. Jornada | 03.04.1999 | VVV | - | Helmond Sport | 0:1 | |
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| 9. Jornada | 10.04.1999 | Helmond Sport | - | RBC Roosendaal | 3:3 | |
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| 9. Jornada | 17.04.1999 | Telstar | - | Helmond Sport | 2:0 |  |
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| 10. Jornada | 01.05.1999 | Heracles Almelo | - | Helmond Sport | 0:1 | ||||
| 10. Jornada | 08.05.1999 | Helmond Sport | - | BV Veendam | 0:2 | ||||
| 10. Jornada | 15.05.1999 | Helmond Sport | - | BV Emmen | 1:0 | ||||
| 10. Jornada | 22.05.1999 | FC Den Bosch | - | Helmond Sport | 4:4 |
Países Bajos