| 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 | Sat 14 Sep 2019 | 2-2 v Oldham AthleticOldham Athletic 2-2 Grimsby Town | Sky Bet League Two |
| 9 | Tue 17 Sep 2019 | 0-1 v Salford CitySalford City 1-0 Grimsby Town | Sky Bet League Two |
| 10 | Sat 21 Sep 2019 | 1-0 v Macclesfield TownGrimsby Town 1-0 Macclesfield Town | Sky Bet League Two |
| 11 | Wed 25 Sep 2019 | 1-7 v ChelseaChelsea 7-1 Grimsby Town | Carabao Cup Third Round |
| 12 | Sat 28 Sep 2019 | 3-1 v Exeter CityExeter City 1-3 Grimsby Town | Sky Bet League Two |
| 13 | Sat 5 Oct 2019 | 0-1 v Mansfield TownGrimsby Town 0-1 Mansfield Town | Sky Bet League Two |
| 14 | Sat 12 Oct 2019 | 1-2 v StevenageStevenage 2-1 Grimsby Town | Sky Bet League Two |
| 15 | Sat 19 Oct 2019 | 0-4 v Leyton OrientGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 16 | Tue 22 Oct 2019 | 0-0 v Cambridge UnitedCambridge United 0-0 Grimsby Town | Sky Bet League Two |
| 17 | Sat 14 Dec 2019 | 0-0 v Carlisle UnitedCarlisle United 0-0 Grimsby Town | Sky Bet League Two |
| 18 | Sat 21 Dec 2019 | 0-1 v Scunthorpe UnitedGrimsby Town 0-1 Scunthorpe United | Sky Bet League Two |
| 19 | Thu 26 Dec 2019 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Grimsby Town | Sky Bet League Two |
| 20 | Sun 29 Dec 2019 | 1-1 v Crawley TownGrimsby Town 1-1 Crawley Town | Sky Bet League Two |
| 21 | Wed 1 Jan 2020 | 1-0 v Salford CityGrimsby Town 1-0 Salford City | Sky Bet League Two |
| 22 | Sat 4 Jan 2020 | 1-0 v Mansfield TownMansfield Town 0-1 Grimsby Town | Sky Bet League Two |
| 23 | Sat 11 Jan 2020 | 1-1 v Leyton OrientLeyton Orient 1-1 Grimsby Town | Sky Bet League Two |
| 24 | Sat 18 Jan 2020 | 0-1 v Exeter CityGrimsby Town 0-1 Exeter City | Sky Bet League Two |
| 25 | Sat 25 Jan 2020 | 2-3 v Crawley TownCrawley Town 3-2 Grimsby Town | Sky Bet League Two |
| 26 | Tue 28 Jan 2020 | 3-1 v StevenageGrimsby Town 3-1 Stevenage | Sky Bet League Two |
| 27 | Sat 1 Feb 2020 | 2-2 v Forest Green RoversGrimsby Town 2-2 Forest Green Rovers | Sky Bet League Two |
| 28 | Sat 8 Feb 2020 | 1-1 v Bradford CityBradford City 1-1 Grimsby Town | Sky Bet League Two |
| 29 | Sat 15 Feb 2020 | 2-1 v MorecambeGrimsby Town 2-1 Morecambe | Sky Bet League Two |
| 30 | Sat 22 Feb 2020 | 1-3 v Swindon TownSwindon Town 3-1 Grimsby Town | Sky Bet League Two |
| 31 | Sat 29 Feb 2020 | 0-3 v Northampton TownGrimsby Town 0-3 Northampton Town | Sky Bet League Two |
| 32 | Tue 3 Mar 2020 | 0-3 v Plymouth ArgylePlymouth Argyle 3-0 Grimsby Town | Sky Bet League Two |
| 33 | Sat 7 Mar 2020 | 2-0 v Scunthorpe UnitedScunthorpe United 0-2 Grimsby Town | Sky Bet League Two |
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