| 1. Round | 22/08/1998 | VVV | - | ADO Den Haag | 2:0 | ||||
| 1. Round | 29/08/1998 | ADO Den Haag | - | Telstar | 2:2 | ||||
| 2. Round | 07/09/1998 | Heracles Almelo | - | ADO Den Haag | 2:2 | ||||
| 2. Round | 20/09/1998 | TOP Oss | - | ADO Den Haag | 0:1 |  |
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| 3. Round | 03/10/1998 | ADO Den Haag | - | Go Ahead Eagles | 1:1 | ||||
| 3. Round | 12/10/1998 | ADO Den Haag | - | FC Volendam | 1:0 |  |
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| 3. Round | 17/10/1998 | ADO Den Haag | - | Helmond Sport | 1:4 | ||||
| 3. Round | 24/10/1998 | RBC Roosendaal | - | ADO Den Haag | 3:1 | ||||
| 3. Round | 31/10/1998 | ADO Den Haag | - | HFC Haarlem | 2:1 | ||||
| 4. Round | 07/11/1998 | BV Veendam | - | ADO Den Haag | 1:0 | ||||
| 4. Round | 23/11/1998 | ADO Den Haag | - | FC Zwolle | 2:1 | |
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| 5. Round | 12/12/1998 | ADO Den Haag | - | VVV | 4:2 | ||||
| 6. Round | 31/01/1999 | ADO Den Haag | - | FC Den Bosch | 1:2 | ||||
| 9. Round | 11/04/1999 | HFC Haarlem | - | ADO Den Haag | 0:1 | ||||
| 9. Round | 17/04/1999 | ADO Den Haag | - | BV Veendam | 1:2 | ||||
| 9. Round | 25/04/1999 | FC Den Bosch | - | ADO Den Haag | 4:1 | ||||
| 10. Round | 01/05/1999 | ADO Den Haag | - | SBV Eindhoven | 2:0 | ||||
| 10. Round | 08/05/1999 | FC Zwolle | - | ADO Den Haag | 2:1 | |
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| 10. Round | 15/05/1999 | ADO Den Haag | - | Dordrecht '90 | 2:1 | |
Netherlands