| 8. Round | 15/09/2018 | Grimsby Town | - | Oldham Athletic | 0:3 | ||||
| 9. Round | 22/09/2018 | Stevenage FC | - | Grimsby Town | 1:0 | ||||
| 10. Round | 29/09/2018 | Grimsby Town | - | Morecambe FC | 1:2 | ||||
| 16. Round | 27/10/2018 | Crewe Alexandra | - | Grimsby Town | 2:0 | ||||
| 17. Round | 03/11/2018 | Cambridge United | - | Grimsby Town | 1:0 | ||||
| 13. Round | 06/11/2018 | Mansfield Town | - | Grimsby Town | 2:1 | ||||
| 18. Round | 17/11/2018 | Grimsby Town | - | Crawley Town | 1:0 | ||||
| 19. Round | 24/11/2018 | Northampton Town | - | Grimsby Town | 2:2 | ||||
| 20. Round | 27/11/2018 | Grimsby Town | - | Tranmere Rovers | 5:2 | ||||
| 21. Round | 08/12/2018 | Cheltenham Town | - | Grimsby Town | 2:1 |  |
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| 22. Round | 15/12/2018 | Grimsby Town | - | Swindon Town | 2:1 | ||||
| 23. Round | 22/12/2018 | Grimsby Town | - | Notts County | 4:0 | ||||
| 24. Round | 26/12/2018 | Port Vale FC | - | Grimsby Town | 0:1 | ||||
| 26. Round | 01/01/2019 | Grimsby Town | - | Mansfield Town | 0:1 | ||||
| 28. Round | 12/01/2019 | Grimsby Town | - | Macclesfield Town | 0:2 |
England