| 2. Round | 26/09/1998 | TOP Oss | - | HFC Haarlem | 4:2 | ||||
| 7. Round | 24/02/1999 | TOP Oss | - | Go Ahead Eagles | 1:2 | ||||
| 7. Round | 27/02/1999 | TOP Oss | - | RBC Roosendaal | 0:3 | ||||
| 8. Round | 06/03/1999 | HFC Haarlem | - | TOP Oss | 1:1 | ||||
| 8. Round | 13/03/1999 | TOP Oss | - | BV Veendam | 2:0 | ||||
| 8. Round | 21/03/1999 | FC Den Bosch | - | TOP Oss | 2:1 |  |
Canada