| 1 | Sat 19 Oct 2019 | 2-0 v Carlisle UnitedPlymouth Argyle 2-0 Carlisle United | Sky Bet League Two |
| 2 | Tue 22 Oct 2019 | 4-0 v Leyton OrientPlymouth Argyle 4-0 Leyton Orient | Sky Bet League Two |
| 3 | Sat 26 Oct 2019 | 0-4 v Exeter CityExeter City 4-0 Plymouth Argyle | Sky Bet League Two |
| 4 | Sat 9 Nov 2019 | 1-0 v Bolton WanderersBolton Wanderers 0-1 Plymouth Argyle | Emirates FA Cup First Round |
| 5 | Sat 7 Dec 2019 | 0-1 v Cambridge UnitedCambridge United 1-0 Plymouth Argyle | Sky Bet League Two |
| 6 | Sat 14 Dec 2019 | 3-0 v MorecambePlymouth Argyle 3-0 Morecambe | Sky Bet League Two |
| 7 | Tue 17 Dec 2019 | 0-1 v Bristol RoversPlymouth Argyle 0-1 Bristol Rovers | Emirates FA Cup Second Round |
| 8 | Thu 26 Dec 2019 | 1-0 v Cheltenham TownCheltenham Town 0-1 Plymouth Argyle | Sky Bet League Two |
| 9 | Sun 29 Dec 2019 | 2-1 v StevenagePlymouth Argyle 2-1 Stevenage | Sky Bet League Two |
| 10 | Wed 1 Jan 2020 | 1-2 v Swindon TownPlymouth Argyle 1-2 Swindon Town | Sky Bet League Two |
| 11 | Sat 18 Jan 2020 | 0-1 v Exeter CityGrimsby Town 0-1 Exeter City | Sky Bet League Two |
| 12 | Sat 25 Jan 2020 | 2-3 v Crawley TownCrawley Town 3-2 Grimsby Town | Sky Bet League Two |
| 13 | Tue 28 Jan 2020 | 3-1 v StevenageGrimsby Town 3-1 Stevenage | Sky Bet League Two |
| 14 | Sat 1 Feb 2020 | 2-2 v Forest Green RoversGrimsby Town 2-2 Forest Green Rovers | Sky Bet League Two |
| 15 | Sat 8 Feb 2020 | 1-1 v Bradford CityBradford City 1-1 Grimsby Town | Sky Bet League Two |
| 16 | Tue 11 Feb 2020 | 3-2 v Colchester UnitedColchester United 2-3 Grimsby Town | Sky Bet League Two |
| 17 | Sat 15 Feb 2020 | 2-1 v MorecambeGrimsby Town 2-1 Morecambe | Sky Bet League Two |
| 18 | Sat 22 Feb 2020 | 1-3 v Swindon TownSwindon Town 3-1 Grimsby Town | Sky Bet League Two |
| 19 | Tue 25 Feb 2020 | 4-2 v Newport CountyGrimsby Town 4-2 Newport County | Sky Bet League Two |
| 20 | Sat 29 Feb 2020 | 0-3 v Northampton TownGrimsby Town 0-3 Northampton Town | Sky Bet League Two |
| 21 | Tue 3 Mar 2020 | 0-3 v Plymouth ArgylePlymouth Argyle 3-0 Grimsby Town | Sky Bet League Two |
| 22 | Sat 7 Mar 2020 | 2-0 v Scunthorpe UnitedScunthorpe United 0-2 Grimsby Town | Sky Bet League Two |
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