| 1. Runde | 10.08.1999 | Carlisle United | - | Grimsby Town | 0:0 | ||||
| 1. Runde | 24.08.1999 | Grimsby Town | - | Carlisle United | 6:0 |  |
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| 2. Runde | 14.09.1999 | Grimsby Town | - | Leyton Orient | 4:1 | |
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| 2. Runde | 21.09.1999 | Leyton Orient | - | Grimsby Town | 1:0 | ||||
| 3. Runde | 13.10.1999 | Leicester City | - | Grimsby Town | 2:0 |
England