| Segunda etapa | 19.09.1989 | Shrewsbury Town | - | Swindon Town | 0:3 |  |
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| Segunda etapa | 03.10.1989 | Swindon Town | - | Shrewsbury Town | 3:1 | |
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| Tercera ronda | 24.10.1989 | Swindon Town | - | Bolton Wanderers | 3:3 | |
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| Tercera ronda | 07.11.1989 | Bolton Wanderers | - | Swindon Town | 1:1 pró. | |
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| Tercera ronda | 14.11.1989 | Bolton Wanderers | - | Swindon Town | 1:1 pró. | ||||
| Tercera ronda | 21.11.1989 | Swindon Town | - | Bolton Wanderers | 2:1 pró. | ||||
| Octavos de final | 29.11.1989 | Swindon Town | - | Southampton | 0:0 | ||||
| Octavos de final | 16.01.1990 | Southampton | - | Swindon Town | 4:2 pró. |
Escocia