1. Round 07/08/1999 Grimsby Town - Stockport County 0:1
2. Round 14/08/1999 Nottingham Forest - Grimsby Town 2:1
4. Round 27/08/1999 Crewe Alexandra - Grimsby Town 1:1
5. Round 30/08/1999 Grimsby Town - Swindon Town 1:0
6. Round 05/09/1999 Port Vale FC - Grimsby Town 3:1
7. Round 11/09/1999 Grimsby Town - Walsall FC 1:0
8. Round 18/09/1999 Crystal Palace - Grimsby Town 3:0
19. Round 20/11/1999 Bolton Wanderers - Grimsby Town 2:0
22. Round 04/12/1999 Stockport County - Grimsby Town 2:1
11. Round 14/12/1999 Grimsby Town - West Bromwich Albion 1:1
23. Round 18/12/1999 Huddersfield Town - Grimsby Town 3:1
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
27. Round 15/01/2000 Grimsby Town - Nottingham Forest 4:3
28. Round 22/01/2000 Fulham FC - Grimsby Town 0:1
29. Round 29/01/2000 Grimsby Town - Crewe Alexandra 1:1
30. Round 05/02/2000 Swindon Town - Grimsby Town 0:1
31. Round 12/02/2000 Grimsby Town - Port Vale FC 2:0 yellow card
32. Round 19/02/2000 Norwich City - Grimsby Town 3:0
33. Round 26/02/2000 Grimsby Town - Crystal Palace 1:0
34. Round 04/03/2000 Walsall FC - Grimsby Town 1:0
36. Round 11/03/2000 Queens Park Rangers - Grimsby Town 1:0
39. Round 27/03/2000 Barnsley FC - Grimsby Town 3:0
42. Round 15/04/2000 Grimsby Town - Manchester City 1:1
43. Round 22/04/2000 Grimsby Town - Blackburn Rovers 0:0
45. Round 29/04/2000 Grimsby Town - Tranmere Rovers 1:2
46. Round 07/05/2000 Birmingham City - Grimsby Town 0:0 yellow card