| 1. Runde | 20.08.1996 | Swansea City | - | Gillingham FC | 0:1 | ||||
| 1. Runde | 03.09.1996 | Gillingham FC | - | Swansea City | 2:0 | ||||
| 2. Runde | 17.09.1996 | Barnsley FC | - | Gillingham FC | 1:1 | ||||
| 2. Runde | 24.09.1996 | Gillingham FC | - | Barnsley FC | 1:0 n.V. | ||||
| 3. Runde | 22.10.1996 | Gillingham FC | - | Coventry City | 2:2 | ||||
| 3. Runde | 13.11.1996 | Coventry City | - | Gillingham FC | 0:1 |  |
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| Achtelfinale | 26.11.1996 | Ipswich Town | - | Gillingham FC | 1:0 |
England