1. Round | 07/08/1999 | Crystal Palace | - | Crewe Alexandra | 1:1 | ||||
3. Round | 21/08/1999 | Walsall FC | - | Crewe Alexandra | 1:4 | ||||
7. Round | 11/09/1999 | Norwich City | - | Crewe Alexandra | 2:1 | ||||
8. Round | 18/09/1999 | Crewe Alexandra | - | Swindon Town | 2:1 | ||||
23. Round | 18/12/1999 | Nottingham Forest | - | Crewe Alexandra | 1:0 | ||||
38. Round | 21/03/2000 | Wolverhampton Wanderers | - | Crewe Alexandra | 2:0 | ||||
40. Round | 01/04/2000 | Crewe Alexandra | - | Nottingham Forest | 0:3 |