1. Round 07/08/1999 Grimsby Town - Stockport County 0:1
2. Round 14/08/1999 Nottingham Forest - Grimsby Town 2:1
3. Round 21/08/1999 Grimsby Town - Fulham FC 1:1
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
9. Round 25/09/1999 Portsmouth FC - Grimsby Town 1:2
12. Round 16/10/1999 Blackburn Rovers - Grimsby Town 1:1
14. Round 23/10/1999 Grimsby Town - Birmingham City 1:1 yellow card
15. Round 26/10/1999 Grimsby Town - Portsmouth FC 1:0
16. Round 30/10/1999 Ipswich Town - Grimsby Town 2:0
17. Round 06/11/1999 Wolverhampton Wanderers - Grimsby Town 3:0
18. Round 12/11/1999 Grimsby Town - Charlton Athletic 2:5
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
23. Round 18/12/1999 Huddersfield Town - Grimsby Town 3:1
24. Round 26/12/1999 Grimsby Town - Barnsley FC 0:3 yellow card
26. Round 03/01/2000 Grimsby Town - Sheffield United 2:2
30. Round 05/02/2000 Swindon Town - Grimsby Town 0:1
31. Round 12/02/2000 Grimsby Town - Port Vale FC 2:0
32. Round 19/02/2000 Norwich City - Grimsby Town 3:0
33. Round 26/02/2000 Grimsby Town - Crystal Palace 1:0 Goal
35. Round 07/03/2000 Grimsby Town - Wolverhampton Wanderers 1:0
36. Round 11/03/2000 Queens Park Rangers - Grimsby Town 1:0
37. Round 18/03/2000 Grimsby Town - Bolton Wanderers 0:1
38. Round 22/03/2000 Charlton Athletic - Grimsby Town 4:0
40. Round 01/04/2000 Grimsby Town - Huddersfield Town 0:0
41. Round 08/04/2000 Sheffield United - Grimsby Town 0:0 yellow card
42. Round 15/04/2000 Grimsby Town - Manchester City 1:1
43. Round 22/04/2000 Grimsby Town - Blackburn Rovers 0:0
44. Round 24/04/2000 West Bromwich Albion - Grimsby Town 2:1
46. Round 07/05/2000 Birmingham City - Grimsby Town 0:0