| 28. Round | 12/01/2019 | Grimsby Town | - | Macclesfield Town | 0:2 |  |
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| 29. Round | 19/01/2019 | Lincoln City | - | Grimsby Town | 1:0 | ||||
| 27. Round | 22/01/2019 | Forest Green Rovers | - | Grimsby Town | 3:0 | ||||
| 31. Round | 02/02/2019 | Grimsby Town | - | Newport County | 3:0 | ||||
| 32. Round | 09/02/2019 | Yeovil Town | - | Grimsby Town | 1:3 | ||||
| 33. Round | 16/02/2019 | Grimsby Town | - | Cheltenham Town | 1:0 | ||||
| 34. Round | 23/02/2019 | Swindon Town | - | Grimsby Town | 1:1 | ||||
| 35. Round | 02/03/2019 | Grimsby Town | - | Cambridge United | 0:2 | ||||
| 36. Round | 09/03/2019 | Crawley Town | - | Grimsby Town | 2:1 | ||||
| 37. Round | 12/03/2019 | Tranmere Rovers | - | Grimsby Town | 4:1 | ||||
| 38. Round | 16/03/2019 | Grimsby Town | - | Northampton Town | 0:0 | ||||
| 39. Round | 23/03/2019 | Grimsby Town | - | Bury FC | 0:0 | ||||
| 40. Round | 30/03/2019 | Oldham Athletic | - | Grimsby Town | 2:0 | ||||
| 42. Round | 13/04/2019 | Morecambe FC | - | Grimsby Town | 1:1 | ||||
| 44. Round | 22/04/2019 | Grimsby Town | - | Carlisle United | 1:0 |
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