| 2. Round | 18/09/1989 | Shrewsbury Town | - | Swindon Town | 0:3 |  |
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| 2. Round | 03/10/1989 | Swindon Town | - | Shrewsbury Town | 3:1 | |
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| 3. Round | 24/10/1989 | Swindon Town | - | Bolton Wanderers | 3:3 | |
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| 3. Round | 06/11/1989 | Bolton Wanderers | - | Swindon Town | 1:1 aet | |
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| 3. Round | 13/11/1989 | Bolton Wanderers | - | Swindon Town | 1:1 aet | ||||
| 3. Round | 20/11/1989 | Swindon Town | - | Bolton Wanderers | 2:1 aet | ||||
| Round of 16 | 29/11/1989 | Swindon Town | - | Southampton FC | 0:0 | ||||
| Round of 16 | 15/01/1990 | Southampton FC | - | Swindon Town | 4:2 aet |
Scotland