1. Round 07/08/1999 Grimsby Town - Stockport County 0:1
2. Round 14/08/1999 Nottingham Forest - Grimsby Town 2:1
6. Round 05/09/1999 Port Vale FC - Grimsby Town 3:1
8. Round 18/09/1999 Crystal Palace - Grimsby Town 3:0
9. Round 25/09/1999 Portsmouth FC - Grimsby Town 1:2
10. Round 02/10/1999 Grimsby Town - Ipswich Town 2:1
12. Round 16/10/1999 Blackburn Rovers - Grimsby Town 1:1
13. Round 19/10/1999 Tranmere Rovers - Grimsby Town 3:2
14. Round 23/10/1999 Grimsby Town - Birmingham City 1:1
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
23. Round 18/12/1999 Huddersfield Town - Grimsby Town 3:1
29. Round 29/01/2000 Grimsby Town - Crewe Alexandra 1:1
30. Round 05/02/2000 Swindon Town - Grimsby Town 0:1
32. Round 19/02/2000 Norwich City - Grimsby Town 3:0
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
40. Round 01/04/2000 Grimsby Town - Huddersfield Town 0:0
41. Round 08/04/2000 Sheffield United - Grimsby Town 0:0
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