1. Round | 09/08/1999 | Southend United | - | Oxford United | 0:2 | ![]() |
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1. Round | 23/08/1999 | Oxford United | - | Southend United | 1:0 | ||||
2. Round | 13/09/1999 | Oxford United | - | Everton FC | 1:1 | ![]() |
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2. Round | 21/09/1999 | Everton FC | - | Oxford United | 0:1 | ||||
3. Round | 11/10/1999 | Tranmere Rovers | - | Oxford United | 2:0 | ![]() |