| 1er tour | 10.08.1999 | Hartlepool United | - | Crewe Alexandra | 3:3 |  |
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| 1er tour | 24.08.1999 | Crewe Alexandra | - | Hartlepool United | 1:0 | ||||
| 2e tour | 14.09.1999 | Crewe Alexandra | - | Ipswich Town | 2:1 | ||||
| 2e tour | 21.09.1999 | Ipswich Town | - | Crewe Alexandra | 1:1 | |
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| 3e tour | 13.10.1999 | Tottenham Hotspur | - | Crewe Alexandra | 3:1 |
Écosse