| 2. Round | 19/09/1989 | York City | - | Southampton FC | 0:1 | ||||
| 2. Round | 03/10/1989 | Southampton FC | - | York City | 2:0 | ||||
| 3. Round | 24/10/1989 | Southampton FC | - | Charlton Athletic | 1:0 | ||||
| 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 |  |
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| Quarter-finals | 23/01/1990 | Southampton FC | - | Oldham Athletic | 2:2 | |
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| Quarter-finals | 30/01/1990 | Oldham Athletic | - | Southampton FC | 2:0 |
England