9. Round | 25/09/1999 | Fulham FC | - | Crewe Alexandra | 3:0 | ||||
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 | ||||
2. Round | 02/11/1999 | Crewe Alexandra | - | Charlton Athletic | 0:2 | ||||
17. Round | 05/11/1999 | Port Vale FC | - | Crewe Alexandra | 1:0 | ||||
19. Round | 20/11/1999 | Portsmouth FC | - | Crewe Alexandra | 0:2 | ||||
20. Round | 23/11/1999 | Crewe Alexandra | - | Blackburn Rovers | 0:0 | ||||
21. Round | 27/11/1999 | Ipswich Town | - | Crewe Alexandra | 2:1 | ||||
22. Round | 04/12/1999 | Crewe Alexandra | - | Crystal Palace | 2:0 | ||||
6. Round | 08/12/1999 | Crewe Alexandra | - | West Bromwich Albion | 2:0 | ||||
18. Round | 14/12/1999 | Crewe Alexandra | - | Wolverhampton Wanderers | 1:0 | ||||
40. Round | 01/04/2000 | Crewe Alexandra | - | Nottingham Forest | 0:3 |