1. Round | 07/08/1999 | Crystal Palace | - | Crewe Alexandra | 1:1 | ||||
3. Round | 21/08/1999 | Walsall FC | - | Crewe Alexandra | 1:4 | ||||
4. Round | 27/08/1999 | Crewe Alexandra | - | Grimsby Town | 1:1 | ||||
5. Round | 30/08/1999 | Birmingham City | - | Crewe Alexandra | 5:1 | ||||
7. Round | 11/09/1999 | Norwich City | - | Crewe Alexandra | 2:1 | ||||
8. Round | 18/09/1999 | Crewe Alexandra | - | Swindon Town | 2:1 | ||||
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 | ||||
14. Round | 23/10/1999 | Crewe Alexandra | - | Barnsley FC | 0:1 | ||||
16. Round | 30/10/1999 | Tranmere Rovers | - | Crewe Alexandra | 2:0 | ||||
2. Round | 02/11/1999 | Crewe Alexandra | - | Charlton Athletic | 0:2 | ||||
19. Round | 20/11/1999 | Portsmouth FC | - | Crewe Alexandra | 0:2 | ||||
20. Round | 23/11/1999 | Crewe Alexandra | - | Blackburn Rovers | 0:0 |