| 1. Round | 24/08/1998 | Telstar | - | Go Ahead Eagles | 2:3 |  |
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| 1. Round | 29/08/1998 | ADO Den Haag | - | Telstar | 2:2 | ||||
| 2. Round | 19/09/1998 | Telstar | - | BV Veendam | 2:3 | ||||
| 2. Round | 26/09/1998 | Telstar | - | SBV Eindhoven | 3:2 | ||||
| 3. Round | 03/10/1998 | FC Zwolle | - | Telstar | 1:1 | ||||
| 3. Round | 17/10/1998 | Telstar | - | Dordrecht '90 | 2:3 | ||||
| 3. Round | 24/10/1998 | FC Groningen | - | Telstar | 0:2 | |
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| 3. Round | 31/10/1998 | Telstar | - | VVV | 0:1 | |
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| 4. Round | 07/11/1998 | Helmond Sport | - | Telstar | 2:1 | |
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| 4. Round | 21/11/1998 | TOP Oss | - | Telstar | 0:0 | ||||
| 4. Round | 28/11/1998 | Telstar | - | FC Volendam | 4:2 | ||||
| 5. Round | 12/12/1998 | Go Ahead Eagles | - | Telstar | 3:3 | |
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| 5. Round | 20/12/1998 | Telstar | - | ADO Den Haag | 0:0 | ||||
| 6. Round | 30/01/1999 | Heracles Almelo | - | Telstar | 2:2 | |
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| 7. Round | 27/02/1999 | Telstar | - | FC Den Bosch | 0:1 | ||||
| 8. Round | 06/03/1999 | SBV Eindhoven | - | Telstar | 3:0 | ||||
| 8. Round | 15/03/1999 | Telstar | - | FC Zwolle | 1:2 | ||||
| 8. Round | 20/03/1999 | Dordrecht '90 | - | Telstar | 4:0 | |
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| 9. Round | 03/04/1999 | Telstar | - | FC Groningen | 0:2 | |
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| 9. Round | 24/04/1999 | Telstar | - | Heracles Almelo | 2:2 |
Netherlands