1. Round | 07/08/1999 | Crystal Palace | - | Crewe Alexandra | 1:1 | ||||
10. Round | 03/10/1999 | Crewe Alexandra | - | Tranmere Rovers | 0:2 | ||||
12. Round | 16/10/1999 | Stockport County | - | Crewe Alexandra | 2:1 | ||||
14. Round | 23/10/1999 | Crewe Alexandra | - | Barnsley FC | 0:1 |