| Segunda etapa | 20.09.1989 | York City | - | Southampton | 0:1 |  |
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| Segunda etapa | 03.10.1989 | Southampton | - | York City | 2:0 | ||||
| Tercera ronda | 24.10.1989 | Southampton | - | Charlton Athletic | 1:0 | ||||
| Octavos de final | 29.11.1989 | Swindon Town | - | Southampton | 0:0 | ||||
| Octavos de final | 16.01.1990 | Southampton | - | Swindon Town | 4:2 pró. | |
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| Cuartos de final | 24.01.1990 | Southampton | - | Oldham Athletic | 2:2 | ||||
| Cuartos de final | 31.01.1990 | Oldham Athletic | - | Southampton | 2:0 |
Inglaterra