| 2. Round | 18/09/1989 | Bolton Wanderers | - | Watford FC | 2:1 | ||||
| 2. Round | 03/10/1989 | Watford FC | - | Bolton Wanderers | 1:1 | ||||
| 3. Round | 24/10/1989 | Swindon Town | - | Bolton Wanderers | 3:3 | ||||
| 3. Round | 06/11/1989 | Bolton Wanderers | - | Swindon Town | 1:1 aet | ||||
| 3. Round | 13/11/1989 | Bolton Wanderers | - | Swindon Town | 1:1 aet | ||||
| 3. Round | 20/11/1989 | Swindon Town | - | Bolton Wanderers | 2:1 aet |
England