13. Round | 19/10/1999 | Tranmere Rovers | - | Grimsby Town | 3:2 | ||||
19. Round | 20/11/1999 | Bolton Wanderers | - | Grimsby Town | 2:0 | ||||
20. Round | 23/11/1999 | Grimsby Town | - | Queens Park Rangers | 2:1 | ||||
21. Round | 28/11/1999 | Grimsby Town | - | Norwich City | 2:1 | ||||
22. Round | 04/12/1999 | Stockport County | - | Grimsby Town | 2:1 | ||||
11. Round | 14/12/1999 | Grimsby Town | - | West Bromwich Albion | 1:1 | ||||
24. Round | 26/12/1999 | Grimsby Town | - | Barnsley FC | 0:3 | ||||
25. Round | 28/12/1999 | Manchester City | - | Grimsby Town | 2:1 | ||||
26. Round | 03/01/2000 | Grimsby Town | - | Sheffield United | 2:2 | ||||
31. Round | 12/02/2000 | Grimsby Town | - | Port Vale FC | 2:0 | ||||
34. Round | 04/03/2000 | Walsall FC | - | Grimsby Town | 1:0 | ||||
45. Round | 29/04/2000 | Grimsby Town | - | Tranmere Rovers | 1:2 |