| 2. Runde | 20.09.1989 | York City | - | Southampton FC | 0:1 | ||||
| 2. Runde | 03.10.1989 | Southampton FC | - | York City | 2:0 | ||||
| 3. Runde | 24.10.1989 | Southampton FC | - | Charlton Athletic | 1:0 | ||||
| Achtelfinale | 29.11.1989 | Swindon Town | - | Southampton FC | 0:0 | ||||
| Achtelfinale | 16.01.1990 | Southampton FC | - | Swindon Town | 4:2 n.V. |  |
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| Viertelfinale | 24.01.1990 | Southampton FC | - | Oldham Athletic | 2:2 | |
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| Viertelfinale | 31.01.1990 | Oldham Athletic | - | Southampton FC | 2:0 |
England