| 1. Journée | 07.08.1999 | Crystal Palace | - | Crewe Alexandra | 1:1 |  |
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| 3. Journée | 21.08.1999 | Walsall FC | - | Crewe Alexandra | 1:4 | ||||
| 7. Journée | 11.09.1999 | Norwich City | - | Crewe Alexandra | 2:1 | ||||
| 8. Journée | 18.09.1999 | Crewe Alexandra | - | Swindon Town | 2:1 | ||||
| 23. Journée | 18.12.1999 | Nottingham Forest | - | Crewe Alexandra | 1:0 | ||||
| 38. Journée | 21.03.2000 | Wolverhampton Wanderers | - | Crewe Alexandra | 2:0 | ||||
| 40. Journée | 01.04.2000 | Crewe Alexandra | - | Nottingham Forest | 0:3 |
Angleterre