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 | ||||
18. Round | 12/11/1999 | Grimsby Town | - | Charlton Athletic | 2:5 | ||||
20. Round | 23/11/1999 | Grimsby Town | - | Queens Park Rangers | 2:1 |