| 1. Round | 06/09/1988 | St Patrick's Athletic | - | Heart of Midlothian | 0:2 | ||||
| 1. Round | 05/10/1988 | Heart of Midlothian | - | St Patrick's Athletic | 2:0 | ||||
| 2. Round | 25/10/1988 | Heart of Midlothian | - | Austria Wien | 0:0 | ||||
| 2. Round | 08/11/1988 | Austria Wien | - | Heart of Midlothian | 0:1 | ||||
| Round of 16 | 22/11/1988 | Heart of Midlothian | - | Velež Mostar | 3:0 |  |
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| Round of 16 | 06/12/1988 | Velež Mostar | - | Heart of Midlothian | 2:1 | ||||
| Quarter-finals | 27/02/1989 | Heart of Midlothian | - | Bayern München | 1:0 | ||||
| Quarter-finals | 14/03/1989 | Bayern München | - | Heart of Midlothian | 2:0 |
Scotland