| 1 | Tue 13 Aug 2019 | 1-0 v Doncaster RoversGrimsby Town 1-0 Doncaster Rovers | Carabao Cup First Round |
| 2 | Sat 31 Aug 2019 | 3-1 v WalsallWalsall 1-3 Grimsby Town | Sky Bet League Two |
| 3 | Sat 14 Sep 2019 | 2-2 v Oldham AthleticOldham Athletic 2-2 Grimsby Town | Sky Bet League Two |
| 4 | Tue 17 Sep 2019 | 0-1 v Salford CitySalford City 1-0 Grimsby Town | Sky Bet League Two |
| 5 | Sat 21 Sep 2019 | 1-0 v Macclesfield TownGrimsby Town 1-0 Macclesfield Town | Sky Bet League Two |
| 6 | Wed 25 Sep 2019 | 1-7 v ChelseaChelsea 7-1 Grimsby Town | Carabao Cup Third Round |
| 7 | Sat 28 Sep 2019 | 3-1 v Exeter CityExeter City 1-3 Grimsby Town | Sky Bet League Two |
| 8 | Sat 5 Oct 2019 | 0-1 v Mansfield TownGrimsby Town 0-1 Mansfield Town | Sky Bet League Two |
| 9 | Sat 19 Oct 2019 | 0-4 v Leyton OrientGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 10 | Tue 22 Oct 2019 | 0-0 v Cambridge UnitedCambridge United 0-0 Grimsby Town | Sky Bet League Two |
| 11 | Sat 9 Nov 2019 | 1-1 v Newport CountyGrimsby Town 1-1 Newport County | Emirates FA Cup First Round |
| 12 | Wed 20 Nov 2019 | 0-2 v Newport CountyNewport County 2-0 Grimsby Town | Emirates FA Cup First Round Replay |
| 13 | Sat 23 Nov 2019 | 0-2 v Northampton TownNorthampton Town 2-0 Grimsby Town | Sky Bet League Two |
| 14 | Tue 26 Nov 2019 | 0-0 v Cheltenham TownGrimsby Town 0-0 Cheltenham Town | Sky Bet League Two |
| 15 | Sat 14 Dec 2019 | 0-0 v Carlisle UnitedCarlisle United 0-0 Grimsby Town | Sky Bet League Two |
| 16 | Sat 21 Dec 2019 | 0-1 v Scunthorpe UnitedGrimsby Town 0-1 Scunthorpe United | Sky Bet League Two |
| 17 | Thu 26 Dec 2019 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Grimsby Town | Sky Bet League Two |
| 18 | Sun 29 Dec 2019 | 1-1 v Crawley TownGrimsby Town 1-1 Crawley Town | Sky Bet League Two |
| 19 | Wed 1 Jan 2020 | 1-0 v Salford CityGrimsby Town 1-0 Salford City | Sky Bet League Two |
| 20 | Sat 4 Jan 2020 | 1-0 v Mansfield TownMansfield Town 0-1 Grimsby Town | Sky Bet League Two |
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