1. Round 07/08/1999 Grimsby Town - Stockport County 0:1
3. Round 21/08/1999 Grimsby Town - Fulham FC 1:1 Goal
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
9. Round 25/09/1999 Portsmouth FC - Grimsby Town 1:2
13. Round 19/10/1999 Tranmere Rovers - Grimsby Town 3:2
15. Round 26/10/1999 Grimsby Town - Portsmouth FC 1:0
16. Round 30/10/1999 Ipswich Town - 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
11. Round 14/12/1999 Grimsby Town - West Bromwich Albion 1:1
25. Round 28/12/1999 Manchester City - Grimsby Town 2:1
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
33. Round 26/02/2000 Grimsby Town - Crystal Palace 1:0 yellow card
34. Round 04/03/2000 Walsall FC - Grimsby Town 1:0
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
39. Round 27/03/2000 Barnsley FC - Grimsby Town 3:0
41. Round 08/04/2000 Sheffield United - Grimsby 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 Goal
45. Round 29/04/2000 Grimsby Town - Tranmere Rovers 1:2
46. Round 07/05/2000 Birmingham City - Grimsby Town 0:0