5. Round | 30/08/1999 | Birmingham City | - | Crewe Alexandra | 5:1 | ||||
9. Round | 25/09/1999 | Fulham FC | - | Crewe Alexandra | 3:0 | ||||
17. Round | 05/11/1999 | Port Vale FC | - | Crewe Alexandra | 1:0 | ||||
23. Round | 18/12/1999 | Nottingham Forest | - | Crewe Alexandra | 1:0 | ||||
24. Round | 26/12/1999 | Crewe Alexandra | - | Huddersfield Town | 1:1 | ||||
25. Round | 28/12/1999 | Queens Park Rangers | - | Crewe Alexandra | 1:0 | ||||
42. Round | 15/04/2000 | Crewe Alexandra | - | Queens Park Rangers | 2:1 | ||||
44. Round | 24/04/2000 | Sheffield United | - | Crewe Alexandra | 1:1 |