1. Round 07/08/1999 Grimsby Town - Stockport County 0:1
2. Round 14/08/1999 Nottingham Forest - Grimsby Town 2:1 yellow card
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 Goal
10. Round 02/10/1999 Grimsby Town - Ipswich Town 2:1 Goal
12. Round 16/10/1999 Blackburn Rovers - Grimsby Town 1:1 Goal
13. Round 19/10/1999 Tranmere Rovers - Grimsby Town 3:2
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 Goal
19. Round 20/11/1999 Bolton Wanderers - Grimsby Town 2:0
20. Round 23/11/1999 Grimsby Town - Queens Park Rangers 2:1 GoalGoal
21. Round 28/11/1999 Grimsby Town - Norwich City 2:1 GoalGoal
22. Round 04/12/1999 Stockport County - Grimsby Town 2:1
24. Round 26/12/1999 Grimsby Town - Barnsley FC 0:3
26. Round 03/01/2000 Grimsby Town - Sheffield United 2:2 Goal yellow card
27. Round 15/01/2000 Grimsby Town - Nottingham Forest 4:3 GoalGoal yellow card
28. Round 22/01/2000 Fulham FC - Grimsby Town 0:1
30. Round 05/02/2000 Swindon Town - Grimsby Town 0:1 Goal
32. Round 19/02/2000 Norwich City - Grimsby Town 3:0 yellow card
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 yellow card
44. Round 24/04/2000 West Bromwich Albion - Grimsby Town 2:1
45. Round 29/04/2000 Grimsby Town - Tranmere Rovers 1:2
46. Round 07/05/2000 Birmingham City - Grimsby Town 0:0