| 13. Jornada | 19.10.1999 | Tranmere Rovers | - | Grimsby Town | 3:2 | ||||
| 19. Jornada | 20.11.1999 | Bolton Wanderers | - | Grimsby Town | 2:0 | ||||
| 20. Jornada | 23.11.1999 | Grimsby Town | - | Queens Park Rangers | 2:1 | ||||
| 21. Jornada | 28.11.1999 | Grimsby Town | - | Norwich City | 2:1 | ||||
| 22. Jornada | 04.12.1999 | Stockport County | - | Grimsby Town | 2:1 | ||||
| 11. Jornada | 14.12.1999 | Grimsby Town | - | West Bromwich Albion | 1:1 | ||||
| 24. Jornada | 26.12.1999 | Grimsby Town | - | Barnsley FC | 0:3 | ||||
| 25. Jornada | 28.12.1999 | Manchester City | - | Grimsby Town | 2:1 | ||||
| 26. Jornada | 03.01.2000 | Grimsby Town | - | Sheffield United | 2:2 | ||||
| 31. Jornada | 12.02.2000 | Grimsby Town | - | Port Vale FC | 2:0 | ||||
| 34. Jornada | 04.03.2000 | Walsall FC | - | Grimsby Town | 1:0 | ||||
| 45. Jornada | 29.04.2000 | Grimsby Town | - | Tranmere Rovers | 1:2 |
Inglaterra