| 1 | Sat 7 Jul 2018 | 31-1 v Folkestone InvictaFolkestone Invicta 1-1 Gillingham | Friendly |
| 2 | Tue 17 Jul 2018 | 33-0 v DartfordDartford 0-3 Gillingham | Friendly |
| 3 | Sat 21 Jul 2018 | 33-0 v Dover AthleticDover Athletic 0-3 Gillingham | Friendly |
| 4 | Tue 24 Jul 2018 | 34-0 v EastleighEastleigh 0-4 Gillingham | Friendly |
| 5 | Tue 24 Jul 2018 | 34-0 v Chatham TownChatham Town 0-4 Gillingham | Friendly |
| 6 | Sat 4 Aug 2018 | 32-0 v Accrington StanleyAccrington Stanley 0-2 Gillingham | Sky Bet League One |
| 7 | Sat 11 Aug 2018 | 33-1 v Burton AlbionGillingham 3-1 Burton Albion | Sky Bet League One |
| 8 | Tue 14 Aug 2018 | 30-0 v MillwallMillwall 0-0 Gillingham | Carabao Cup First Round |
| 9 | Sat 18 Aug 2018 | 31-2 v WalsallWalsall 2-1 Gillingham | Sky Bet League One |
| 10 | Wed 22 Aug 2018 | 31-4 v SunderlandGillingham 1-4 Sunderland | Sky Bet League One |
| 11 | Sat 25 Aug 2018 | 3 1-1 v Coventry CityGillingham 1-1 Coventry City | Sky Bet League One |
| 12 | Sat 1 Sep 2018 | 31-2 v BarnsleyBarnsley 2-1 Gillingham | Sky Bet League One |
| 13 | Sat 8 Sep 2018 | 3 0-1 v AFC WimbledonGillingham 0-1 AFC Wimbledon | Sky Bet League One |
| 14 | Sat 15 Sep 2018 | 30-3 v RochdaleRochdale 3-0 Gillingham | Sky Bet League One |
| 15 | Sat 29 Sep 2018 | 3 2-2 v Shrewsbury TownShrewsbury Town 2-2 Gillingham | Sky Bet League One |
| 16 | Sat 13 Oct 2018 | 30-2 v Southend UnitedGillingham 0-2 Southend United | Sky Bet League One |
| 17 | Tue 23 Oct 2018 | 31-3 v Plymouth ArgylePlymouth Argyle 3-1 Gillingham | Sky Bet League One |
| 18 | Tue 13 Nov 2018 | 32-1 v Crawley TownGillingham 2-1 Crawley Town | Checkatrade Trophy Southern Group A |
| 19 | Wed 21 Nov 2018 | 34-3 v Hartlepool UnitedHartlepool United 3-4 Gillingham | Emirates FA Cup First Round Replay |
| 20 | Sat 24 Nov 2018 | 31-3 v Luton TownGillingham 1-3 Luton Town | Sky Bet League One |
| 21 | Tue 27 Nov 2018 | 32-1 v Bristol RoversBristol Rovers 1-2 Gillingham | Sky Bet League One |
| 22 | Sun 2 Dec 2018 | 31-0 v Slough TownSlough Town 0-1 Gillingham | Emirates FA Cup Second Round |
| 23 | Sat 15 Dec 2018 | 3 2-2 v Wycombe WanderersGillingham 2-2 Wycombe Wanderers | Sky Bet League One |
| 24 | Tue 1 Jan 2019 | 30-2 v Southend UnitedSouthend United 2-0 Gillingham | Sky Bet League One |
| 25 | Sat 5 Jan 2019 | 31-0 v Cardiff CityGillingham 1-0 Cardiff City | Emirates FA Cup Third Round |
| 26 | Sat 12 Jan 2019 | 33-2 v Burton AlbionBurton Albion 2-3 Gillingham | Sky Bet League One |
| 27 | Sat 19 Jan 2019 | 30-3 v WalsallGillingham 0-3 Walsall | Sky Bet League One |
| 28 | Sat 26 Jan 2019 | 31-4 v Swansea CitySwansea City 4-1 Gillingham | Emirates FA Cup Fourth Round |
| 29 | Mon 22 Apr 2019 | 31-1 v Bradford CityBradford City 1-1 Gillingham | Sky Bet League One |
| 30 | Sat 4 May 2019 | 3 3-0 v BlackpoolBlackpool 0-3 Gillingham | Sky Bet League One |
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