4. Round | 27/08/1999 | Crewe Alexandra | - | Grimsby Town | 1:1 | ||||
5. Round | 30/08/1999 | Birmingham City | - | Crewe Alexandra | 5:1 | ||||
9. Round | 25/09/1999 | Fulham FC | - | Crewe Alexandra | 3:0 | ||||
10. Round | 03/10/1999 | Crewe Alexandra | - | Tranmere Rovers | 0:2 | ||||
11. Round | 09/10/1999 | Crewe Alexandra | - | Sheffield United | 1:0 | ||||
12. Round | 16/10/1999 | Stockport County | - | Crewe Alexandra | 2:1 | ||||
13. Round | 19/10/1999 | Bolton Wanderers | - | Crewe Alexandra | 2:2 | ||||
30. Round | 05/02/2000 | Crewe Alexandra | - | Birmingham City | 2:3 | ||||
31. Round | 12/02/2000 | West Bromwich Albion | - | Crewe Alexandra | 1:0 | ||||
32. Round | 19/02/2000 | Crewe Alexandra | - | Ipswich Town | 1:2 | ||||
33. Round | 26/02/2000 | Swindon Town | - | Crewe Alexandra | 0:1 | ||||
43. Round | 22/04/2000 | Crewe Alexandra | - | Stockport County | 3:2 | ||||
44. Round | 24/04/2000 | Sheffield United | - | Crewe Alexandra | 1:1 |