| 1 | 3/8/2019 | 2-0 v MorecambeMorecambe 0-2 Grimsby Town | Sky Bet League Two |
| 2 | 13/8/2019 | 1-0 v Doncaster RoversGrimsby Town 1-0 Doncaster Rovers | Carabao Cup First Round |
| 3 | 17/8/2019 | 0-1 v Forest Green RoversForest Green Rovers 1-0 Grimsby Town | Sky Bet League Two |
| 4 | 20/8/2019 | 2-2 v Colchester UnitedGrimsby Town 2-2 Colchester United | Sky Bet League Two |
| 5 | 24/8/2019 | 5-2 v Port ValeGrimsby Town 5-2 Port Vale | Sky Bet League Two |
| 6 | 31/8/2019 | 3-1 v WalsallWalsall 1-3 Grimsby Town | Sky Bet League Two |
| 7 | 7/9/2019 | 0-2 v Crewe AlexandraGrimsby Town 0-2 Crewe Alexandra | Sky Bet League Two |
| 8 | 14/9/2019 | 2-2 v Oldham AthleticOldham Athletic 2-2 Grimsby Town | Sky Bet League Two |
| 9 | 17/9/2019 | 0-1 v Salford CitySalford City 1-0 Grimsby Town | Sky Bet League Two |
| 10 | 21/9/2019 | 1-0 v Macclesfield TownGrimsby Town 1-0 Macclesfield Town | Sky Bet League Two |
| 11 | 25/9/2019 | 1-7 v ChelseaChelsea 7-1 Grimsby Town | Carabao Cup Third Round |
| 12 | 28/9/2019 | 3-1 v Exeter CityExeter City 1-3 Grimsby Town | Sky Bet League Two |
| 13 | 5/10/2019 | 0-1 v Mansfield TownGrimsby Town 0-1 Mansfield Town | Sky Bet League Two |
| 14 | 8/10/2019 | 2-3 v SunderlandSunderland 3-2 Grimsby Town | Checkatrade Trophy Northern Group A |
| 15 | 12/10/2019 | 1-2 v StevenageStevenage 2-1 Grimsby Town | Sky Bet League Two |
| 16 | 19/10/2019 | 0-4 v Leyton OrientGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 17 | 22/10/2019 | 0-0 v Cambridge UnitedCambridge United 0-0 Grimsby Town | Sky Bet League Two |
| 18 | 9/11/2019 | 1-1 v Newport CountyGrimsby Town 1-1 Newport County | Emirates FA Cup First Round |
| 19 | 20/11/2019 | 0-2 v Newport CountyNewport County 2-0 Grimsby Town | Emirates FA Cup First Round Replay |
| 20 | 26/11/2019 | 0-0 v Cheltenham TownGrimsby Town 0-0 Cheltenham Town | Sky Bet League Two |
