| 1 | Sat 3 Aug 2019 | 2-0 v MorecambeMorecambe 0-2 Grimsby Town | Sky Bet League Two |
| 2 | Tue 13 Aug 2019 | 1-0 v Doncaster RoversGrimsby Town 1-0 Doncaster Rovers | Carabao Cup First Round |
| 3 | Sat 17 Aug 2019 | 0-1 v Forest Green RoversForest Green Rovers 1-0 Grimsby Town | Sky Bet League Two |
| 4 | Tue 20 Aug 2019 | 2-2 v Colchester UnitedGrimsby Town 2-2 Colchester United | Sky Bet League Two |
| 5 | Sat 24 Aug 2019 | 5-2 v Port ValeGrimsby Town 5-2 Port Vale | Sky Bet League Two |
| 6 | Sat 31 Aug 2019 | 3-1 v WalsallWalsall 1-3 Grimsby Town | Sky Bet League Two |
| 7 | Sat 7 Sep 2019 | 0-2 v Crewe AlexandraGrimsby Town 0-2 Crewe Alexandra | Sky Bet League Two |
| 8 | Tue 17 Sep 2019 | 0-1 v Salford CitySalford City 1-0 Grimsby Town | Sky Bet League Two |
| 9 | Sat 21 Sep 2019 | 1-0 v Macclesfield TownGrimsby Town 1-0 Macclesfield Town | Sky Bet League Two |
| 10 | Wed 25 Sep 2019 | 1-7 v ChelseaChelsea 7-1 Grimsby Town | Carabao Cup Third Round |
| 11 | Sat 5 Oct 2019 | 0-1 v Mansfield TownGrimsby Town 0-1 Mansfield Town | Sky Bet League Two |
| 12 | Tue 8 Oct 2019 | 2-3 v SunderlandSunderland 3-2 Grimsby Town | Leasing.com Trophy Northern Group A |
| 13 | Sat 12 Oct 2019 | 1-2 v StevenageStevenage 2-1 Grimsby Town | Sky Bet League Two |
| 14 | Sat 19 Oct 2019 | 0-4 v Leyton OrientGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 15 | Tue 22 Oct 2019 | 0-0 v Cambridge UnitedCambridge United 0-0 Grimsby Town | Sky Bet League Two |
| 16 | Sat 9 Nov 2019 | 1-1 v Newport CountyGrimsby Town 1-1 Newport County | Emirates FA Cup First Round |
| 17 | Wed 20 Nov 2019 | 0-2 v Newport CountyNewport County 2-0 Grimsby Town | Emirates FA Cup First Round Replay |
| 18 | Sat 23 Nov 2019 | 0-2 v Northampton TownNorthampton Town 2-0 Grimsby Town | Sky Bet League Two |
| 19 | Tue 26 Nov 2019 | 0-0 v Cheltenham TownGrimsby Town 0-0 Cheltenham Town | Sky Bet League Two |
| 20 | Sat 14 Dec 2019 | 0-0 v Carlisle UnitedCarlisle United 0-0 Grimsby Town | Sky Bet League Two |
| 21 | Sat 21 Dec 2019 | 0-1 v Scunthorpe UnitedGrimsby Town 0-1 Scunthorpe United | Sky Bet League Two |
| 22 | Sun 29 Dec 2019 | 1-1 v Crawley TownGrimsby Town 1-1 Crawley Town | Sky Bet League Two |
| 23 | Tue 28 Jan 2020 | 3-1 v StevenageGrimsby Town 3-1 Stevenage | Sky Bet League Two |
| 24 | Sat 1 Feb 2020 | 2-2 v Forest Green RoversGrimsby Town 2-2 Forest Green Rovers | Sky Bet League Two |
| 25 | Sat 8 Feb 2020 | 1-1 v Bradford CityBradford City 1-1 Grimsby Town | Sky Bet League Two |
| 26 | Tue 11 Feb 2020 | 3-2 v Colchester UnitedColchester United 2-3 Grimsby Town | Sky Bet League Two |
| 27 | Sat 15 Feb 2020 | 2-1 v MorecambeGrimsby Town 2-1 Morecambe | Sky Bet League Two |
| 28 | Sat 22 Feb 2020 | 1-3 v Swindon TownSwindon Town 3-1 Grimsby Town | Sky Bet League Two |
| 29 | Tue 25 Feb 2020 | 4-2 v Newport CountyGrimsby Town 4-2 Newport County | Sky Bet League Two |
| 30 | Sat 29 Feb 2020 | 0-3 v Northampton TownGrimsby Town 0-3 Northampton Town | Sky Bet League Two |
| 31 | Tue 3 Mar 2020 | 0-3 v Plymouth ArgylePlymouth Argyle 3-0 Grimsby Town | Sky Bet League Two |
| 32 | Sat 7 Mar 2020 | 2-0 v Scunthorpe UnitedScunthorpe United 0-2 Grimsby Town | Sky Bet League Two |
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