| 1 | Sat 7 Jul 2018 | 61-1 v Folkestone InvictaFolkestone Invicta 1-1 Gillingham | Friendly |
| 2 | Tue 10 Jul 2018 | 65-1 v BromleyBromley 1-5 Gillingham | Friendly |
| 3 | Tue 17 Jul 2018 | 63-0 v DartfordDartford 0-3 Gillingham | Friendly |
| 4 | Sat 21 Jul 2018 | 63-0 v Dover AthleticDover Athletic 0-3 Gillingham | Friendly |
| 5 | Tue 24 Jul 2018 | 64-0 v EastleighEastleigh 0-4 Gillingham | Friendly |
| 6 | Tue 24 Jul 2018 | 64-0 v Chatham TownChatham Town 0-4 Gillingham | Friendly |
| 7 | Sat 4 Aug 2018 | 62-0 v Accrington StanleyAccrington Stanley 0-2 Gillingham | Sky Bet League One |
| 8 | Sat 11 Aug 2018 | 63-1 v Burton AlbionGillingham 3-1 Burton Albion | Sky Bet League One |
| 9 | Sat 18 Aug 2018 | 61-2 v WalsallWalsall 2-1 Gillingham | Sky Bet League One |
| 10 | Wed 22 Aug 2018 | 61-4 v SunderlandGillingham 1-4 Sunderland | Sky Bet League One |
| 11 | Sat 25 Aug 2018 | 6 1-1 v Coventry CityGillingham 1-1 Coventry City | Sky Bet League One |
| 12 | Sat 1 Sep 2018 | 61-2 v BarnsleyBarnsley 2-1 Gillingham | Sky Bet League One |
| 13 | Sat 22 Sep 2018 | 62-4 v Peterborough UnitedGillingham 2-4 Peterborough United | Sky Bet League One |
| 14 | Sat 29 Sep 2018 | 62-2 v Shrewsbury TownShrewsbury Town 2-2 Gillingham | Sky Bet League One |
| 15 | Sat 6 Oct 2018 | 62-0 v PortsmouthPortsmouth 0-2 Gillingham | Sky Bet League One |
| 16 | Sat 13 Oct 2018 | 60-2 v Southend UnitedGillingham 0-2 Southend United | Sky Bet League One |
| 17 | Sat 20 Oct 2018 | 6 3-3 v Doncaster RoversDoncaster Rovers 3-3 Gillingham | Sky Bet League One |
| 18 | Tue 23 Oct 2018 | 61-3 v Plymouth ArgylePlymouth Argyle 3-1 Gillingham | Sky Bet League One |
| 19 | Sat 27 Oct 2018 | 64-0 v Bradford CityGillingham 4-0 Bradford City | Sky Bet League One |
| 20 | Sat 3 Nov 2018 | 63-0 v Fleetwood TownGillingham 3-0 Fleetwood Town | Sky Bet League One |
| 21 | Tue 6 Nov 2018 | 60-1 v BlackpoolGillingham 0-1 Blackpool | Sky Bet League One |
| 22 | Sat 10 Nov 2018 | 60-0 v Hartlepool UnitedGillingham 0-0 Hartlepool United | Emirates FA Cup First Round |
| 23 | Sat 17 Nov 2018 | 6 0-1 v Oxford UnitedOxford United 1-0 Gillingham | Sky Bet League One |
| 24 | Wed 21 Nov 2018 | 64-3 v Hartlepool UnitedHartlepool United 3-4 Gillingham | Emirates FA Cup First Round Replay |
| 25 | Sat 24 Nov 2018 | 61-3 v Luton TownGillingham 1-3 Luton Town | Sky Bet League One |
| 26 | Tue 27 Nov 2018 | 62-1 v Bristol RoversBristol Rovers 1-2 Gillingham | Sky Bet League One |
| 27 | Sun 2 Dec 2018 | 61-0 v Slough TownSlough Town 0-1 Gillingham | Emirates FA Cup Second Round |
| 28 | Sat 8 Dec 2018 | 62-0 v Scunthorpe UnitedScunthorpe United 0-2 Gillingham | Sky Bet League One |
| 29 | Sat 15 Dec 2018 | 62-2 v Wycombe WanderersGillingham 2-2 Wycombe Wanderers | Sky Bet League One |
| 30 | Sat 22 Dec 2018 | 60-2 v Charlton AthleticCharlton Athletic 2-0 Gillingham | Sky Bet League One |
| 31 | Wed 26 Dec 2018 | 62-0 v PortsmouthGillingham 2-0 Portsmouth | Sky Bet League One |
| 32 | Sat 29 Dec 2018 | 61-3 v Doncaster RoversGillingham 1-3 Doncaster Rovers | Sky Bet League One |
| 33 | Tue 1 Jan 2019 | 60-2 v Southend UnitedSouthend United 2-0 Gillingham | Sky Bet League One |
| 34 | Sat 5 Jan 2019 | 6 1-0 v Cardiff CityGillingham 1-0 Cardiff City | Emirates FA Cup Third Round |
| 35 | Sat 12 Jan 2019 | 63-2 v Burton AlbionBurton Albion 2-3 Gillingham | Sky Bet League One |
| 36 | Sat 19 Jan 2019 | 60-3 v WalsallGillingham 0-3 Walsall | Sky Bet League One |
| 37 | Sat 26 Jan 2019 | 61-4 v Swansea CitySwansea City 4-1 Gillingham | Emirates FA Cup Fourth Round |
| 38 | Tue 29 Jan 2019 | 60-0 v Accrington StanleyGillingham 0-0 Accrington Stanley | Sky Bet League One |
| 39 | Sat 2 Feb 2019 | 61-1 v Coventry CityCoventry City 1-1 Gillingham | Sky Bet League One |
| 40 | Sat 9 Feb 2019 | 6 1-4 v BarnsleyGillingham 1-4 Barnsley | Sky Bet League One |
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