| 1. Runde | 10.08.1999 | Southend United | - | Oxford United | 0:2 |  |
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| 1. Runde | 24.08.1999 | Oxford United | - | Southend United | 1:0 | ||||
| 2. Runde | 14.09.1999 | Oxford United | - | Everton FC | 1:1 | |
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| 2. Runde | 22.09.1999 | Everton FC | - | Oxford United | 0:1 | ||||
| 3. Runde | 12.10.1999 | Tranmere Rovers | - | Oxford United | 2:0 |  |
England