| 1. Round | 11/09/1968 | K. Beerschot VAV | - | DWS Amsterdam | 1:1 | ||||
| 1. Round | 25/09/1968 | DWS Amsterdam | - | K. Beerschot VAV | 2:1 |  |
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| 2. Round | 23/10/1968 | Chelsea FC | - | DWS Amsterdam | 0:0 | ||||
| 2. Round | 30/10/1968 | DWS Amsterdam | - | Chelsea FC | 0:0 aet | ||||
| Round of 16 | 15/01/1969 | DWS Amsterdam | - | Rangers FC | 0:2 | ||||
| Round of 16 | 22/01/1969 | Rangers FC | - | DWS Amsterdam | 2:1 |
Netherlands