| 1 | Sat 15 Sep 2018 | 0-3 v Oldham AthleticGrimsby Town 0-3 Oldham Athletic | Sky Bet League Two |
| 2 | Sat 22 Sep 2018 | 0-1 v StevenageStevenage 1-0 Grimsby Town | Sky Bet League Two |
| 3 | Sat 29 Sep 2018 | 1-2 v MorecambeGrimsby Town 1-2 Morecambe | Sky Bet League Two |
| 4 | Tue 9 Oct 2018 | 30 0-2 v Doncaster RoversDoncaster Rovers 2-0 Grimsby Town | Checkatrade Trophy Northern Group G |
| 5 | Sat 27 Oct 2018 | 0-2 v Crewe AlexandraCrewe Alexandra 2-0 Grimsby Town | Sky Bet League Two |
| 6 | Sat 3 Nov 2018 | 300-1 v Cambridge UnitedCambridge United 1-0 Grimsby Town | Sky Bet League Two |
| 7 | Tue 6 Nov 2018 | 301-2 v Mansfield TownMansfield Town 2-1 Grimsby Town | Sky Bet League Two |
| 8 | Sat 10 Nov 2018 | 303-1 v Milton Keynes DonsGrimsby Town 3-1 Milton Keynes Dons | Emirates FA Cup First Round |
| 9 | Sat 17 Nov 2018 | 301-0 v Crawley TownGrimsby Town 1-0 Crawley Town | Sky Bet League Two |
| 10 | Sat 24 Nov 2018 | 302-2 v Northampton TownNorthampton Town 2-2 Grimsby Town | Sky Bet League Two |
| 11 | Tue 27 Nov 2018 | 305-2 v Tranmere RoversGrimsby Town 5-2 Tranmere Rovers | Sky Bet League Two |
| 12 | Sun 2 Dec 2018 | 302-0 v ChesterfieldChesterfield 0-2 Grimsby Town | Emirates FA Cup Second Round |
| 13 | Sat 8 Dec 2018 | 30 1-2 v Cheltenham TownCheltenham Town 2-1 Grimsby Town | Sky Bet League Two |
| 14 | Sat 15 Dec 2018 | 302-1 v Swindon TownGrimsby Town 2-1 Swindon Town | Sky Bet League Two |
| 15 | Sat 22 Dec 2018 | 304-0 v Notts CountyGrimsby Town 4-0 Notts County | Sky Bet League Two |
| 16 | Wed 26 Dec 2018 | 301-0 v Port ValePort Vale 0-1 Grimsby Town | Sky Bet League Two |
| 17 | Tue 1 Jan 2019 | 300-1 v Mansfield TownGrimsby Town 0-1 Mansfield Town | Sky Bet League Two |
| 18 | Sat 12 Jan 2019 | 300-2 v Macclesfield TownGrimsby Town 0-2 Macclesfield Town | Sky Bet League Two |
| 19 | Sat 26 Jan 2019 | 0-3 v Mansfield TownMansfield Town 3-0 Tranmere Rovers | Sky Bet League Two |
| 20 | Tue 5 Feb 2019 | 1-2 v Northampton TownTranmere Rovers 1-2 Northampton Town | Sky Bet League Two |
| 21 | Sat 9 Feb 2019 | 2-0 v StevenageTranmere Rovers 2-0 Stevenage | Sky Bet League Two |
| 22 | Sat 16 Feb 2019 | 0-0 v Cambridge UnitedCambridge United 0-0 Tranmere Rovers | Sky Bet League Two |
| 23 | Tue 19 Feb 2019 | 2-1 v Port ValePort Vale 1-2 Tranmere Rovers | Sky Bet League Two |
| 24 | Sat 23 Feb 2019 | 1-0 v Notts CountyTranmere Rovers 1-0 Notts County | Sky Bet League Two |
| 25 | Sat 2 Mar 2019 | 1-0 v Exeter CityExeter City 0-1 Tranmere Rovers | Sky Bet League Two |
| 26 | Fri 8 Mar 2019 | 1-0 v Crewe AlexandraTranmere Rovers 1-0 Crewe Alexandra | Sky Bet League Two |
| 27 | Tue 12 Mar 2019 | 4-1 v Grimsby TownTranmere Rovers 4-1 Grimsby Town | Sky Bet League Two |
| 28 | Sat 23 Mar 2019 | 2-0 v Colchester UnitedColchester United 0-2 Tranmere Rovers | Sky Bet League Two |
| 29 | Sat 13 Apr 2019 | 2-1 v Milton Keynes DonsTranmere Rovers 2-1 Milton Keynes Dons | Sky Bet League Two |
| 30 | Fri 19 Apr 2019 | 0-1 v Forest Green RoversTranmere Rovers 0-1 Forest Green Rovers | Sky Bet League Two |
| 31 | Tue 30 Apr 2019 | 1-1 v BuryTranmere Rovers 1-1 Bury | Sky Bet League Two |
| 32 | Sat 25 May 2019 | 1-0 v Newport CountyNewport County 0-1 Tranmere Rovers | Sky Bet League Two Play-off Final |
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