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 | ||||
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 | ||||
17. Round | 06/11/1999 | Wolverhampton Wanderers | - | Grimsby Town | 3:0 | ||||
18. Round | 12/11/1999 | Grimsby Town | - | Charlton Athletic | 2:5 | ||||
11. Round | 14/12/1999 | Grimsby Town | - | West Bromwich Albion | 1:1 | ||||
23. Round | 18/12/1999 | Huddersfield Town | - | Grimsby Town | 3:1 |