| 2. Runde | 19.09.1989 | Shrewsbury Town | - | Swindon Town | 0:3 |  |
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| 2. Runde | 03.10.1989 | Swindon Town | - | Shrewsbury Town | 3:1 | ||||
| 3. Runde | 24.10.1989 | Swindon Town | - | Bolton Wanderers | 3:3 |  |
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| 3. Runde | 07.11.1989 | Bolton Wanderers | - | Swindon Town | 1:1 n.V. | ||||
| 3. Runde | 14.11.1989 | Bolton Wanderers | - | Swindon Town | 1:1 n.V. | |
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| 3. Runde | 21.11.1989 | Swindon Town | - | Bolton Wanderers | 2:1 n.V. | |
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| Achtelfinale | 29.11.1989 | Swindon Town | - | Southampton FC | 0:0 | ||||
| Achtelfinale | 16.01.1990 | Southampton FC | - | Swindon Town | 4:2 n.V. |
Schottland