| 6. Round | 30/01/1999 | Heracles Almelo | - | Telstar | 2:2 | ||||
| 7. Round | 06/02/1999 | RBC Roosendaal | - | Telstar | 3:0 | ||||
| 7. Round | 14/02/1999 | Telstar | - | HFC Haarlem | 1:3 | ||||
| 8. Round | 06/03/1999 | SBV Eindhoven | - | Telstar | 3:0 | ||||
| 8. Round | 27/03/1999 | BV Veendam | - | Telstar | 1:1 | ||||
| 9. Round | 03/04/1999 | Telstar | - | FC Groningen | 0:2 | ||||
| 9. Round | 10/04/1999 | VVV | - | Telstar | 3:3 | ||||
| 9. Round | 17/04/1999 | Telstar | - | Helmond Sport | 2:0 | ||||
| 10. Round | 01/05/1999 | BV Emmen | - | Telstar | 2:1 |
Netherlands