1. Round 07/08/1999 Grimsby Town - Stockport County 0:1
2. Round 14/08/1999 Nottingham Forest - Grimsby Town 2:1 yellow card
6. Round 05/09/1999 Port Vale FC - Grimsby Town 3:1 Goal
7. Round 11/09/1999 Grimsby Town - Walsall FC 1:0 Goal
8. Round 18/09/1999 Crystal Palace - Grimsby Town 3:0
12. Round 16/10/1999 Blackburn Rovers - Grimsby Town 1:1
13. Round 19/10/1999 Tranmere Rovers - Grimsby Town 3:2 GoalGoal
14. Round 23/10/1999 Grimsby Town - Birmingham City 1:1 Goal
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
22. Round 04/12/1999 Stockport County - Grimsby Town 2:1
11. Round 14/12/1999 Grimsby Town - West Bromwich Albion 1:1 Goal
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 Goal
30. Round 05/02/2000 Swindon Town - Grimsby Town 0:1
31. Round 12/02/2000 Grimsby Town - Port Vale FC 2:0 Goal
32. Round 19/02/2000 Norwich City - Grimsby Town 3:0
38. Round 22/03/2000 Charlton Athletic - Grimsby Town 4:0
39. Round 27/03/2000 Barnsley FC - Grimsby Town 3:0
40. Round 01/04/2000 Grimsby Town - Huddersfield Town 0:0
43. Round 22/04/2000 Grimsby Town - Blackburn Rovers 0:0
44. Round 24/04/2000 West Bromwich Albion - Grimsby Town 2:1
45. Round 29/04/2000 Grimsby Town - Tranmere Rovers 1:2