| 1 | 7/7/2018 | 131-1 v Folkestone InvictaFolkestone Invicta 1-1 Gillingham | Friendly |
| 2 | 10/7/2018 | 135-1 v Faversham TownFaversham Town 1-5 Gillingham | Friendly |
| 3 | 17/7/2018 | 13-0 v DartfordDartford 0-3 Gillingham | Friendly |
| 4 | 21/7/2018 | 13-0 v Dover AthleticDover Athletic 0-3 Gillingham | Friendly |
| 5 | 24/7/2018 | 14-0 v EastleighEastleigh 0-4 Gillingham | Friendly |
| 6 | 24/7/2018 | 14-0 v Chatham TownChatham Town 0-4 Gillingham | Friendly |
| 7 | 4/8/2018 | 12-0 v Accrington StanleyAccrington Stanley 0-2 Gillingham | Sky Bet League One |
| 8 | 11/8/2018 | 13-1 v Burton AlbionGillingham 3-1 Burton Albion | Sky Bet League One |
| 9 | 14/8/2018 | 10-0 v MillwallMillwall 0-0 Gillingham | Carabao Cup First Round |
| 10 | 18/8/2018 | 11-2 v WalsallWalsall 2-1 Gillingham | Sky Bet League One |
| 11 | 22/8/2018 | 11-4 v SunderlandGillingham 1-4 Sunderland | Sky Bet League One |
| 12 | 25/8/2018 | 11-1 v Coventry CityGillingham 1-1 Coventry City | Sky Bet League One |
| 13 | 1/9/2018 | 11-2 v BarnsleyBarnsley 2-1 Gillingham | Sky Bet League One |
| 14 | 8/9/2018 | 10-1 v AFC WimbledonGillingham 0-1 AFC Wimbledon | Sky Bet League One |
| 15 | 15/9/2018 | 10-3 v RochdaleRochdale 3-0 Gillingham | Sky Bet League One |
| 16 | 22/9/2018 | 12-4 v Peterborough UnitedGillingham 2-4 Peterborough United | Sky Bet League One |
| 17 | 29/9/2018 | 12-2 v Shrewsbury TownShrewsbury Town 2-2 Gillingham | Sky Bet League One |
| 18 | 6/10/2018 | 12-0 v PortsmouthPortsmouth 0-2 Gillingham | Sky Bet League One |
| 19 | 13/10/2018 | 10-2 v Southend UnitedGillingham 0-2 Southend United | Sky Bet League One |
| 20 | 20/10/2018 | 13-3 v Doncaster RoversDoncaster Rovers 3-3 Gillingham | Sky Bet League One |
| 21 | 23/10/2018 | 11-3 v Plymouth ArgylePlymouth Argyle 3-1 Gillingham | Sky Bet League One |
| 22 | 27/10/2018 | 14-0 v Bradford CityGillingham 4-0 Bradford City | Sky Bet League One |
| 23 | 3/11/2018 | 13-0 v Fleetwood TownGillingham 3-0 Fleetwood Town | Sky Bet League One |
| 24 | 6/11/2018 | 10-1 v BlackpoolGillingham 0-1 Blackpool | Sky Bet League One |
| 25 | 10/11/2018 | 10-0 v Hartlepool UnitedGillingham 0-0 Hartlepool United | Emirates FA Cup First Round |
| 26 | 17/11/2018 | 10-1 v Oxford UnitedOxford United 1-0 Gillingham | Sky Bet League One |
| 27 | 21/11/2018 | 14-3 v Hartlepool UnitedHartlepool United 3-4 Gillingham | Emirates FA Cup First Round Replay |
| 28 | 24/11/2018 | 11-3 v Luton TownGillingham 1-3 Luton Town | Sky Bet League One |
| 29 | 27/11/2018 | 1 2-1 v Bristol RoversBristol Rovers 1-2 Gillingham | Sky Bet League One |
| 30 | 2/12/2018 | 11-0 v Slough TownSlough Town 0-1 Gillingham | Emirates FA Cup Second Round |
| 31 | 8/12/2018 | 12-0 v Scunthorpe UnitedScunthorpe United 0-2 Gillingham | Sky Bet League One |
| 32 | 15/12/2018 | 12-2 v Wycombe WanderersGillingham 2-2 Wycombe Wanderers | Sky Bet League One |
| 33 | 22/12/2018 | 10-2 v Charlton AthleticCharlton Athletic 2-0 Gillingham | Sky Bet League One |
| 34 | 26/12/2018 | 12-0 v PortsmouthGillingham 2-0 Portsmouth | Sky Bet League One |
| 35 | 29/12/2018 | 11-3 v Doncaster RoversGillingham 1-3 Doncaster Rovers | Sky Bet League One |
| 36 | 1/1/2019 | 10-2 v Southend UnitedSouthend United 2-0 Gillingham | Sky Bet League One |
| 37 | 5/1/2019 | 11-0 v Cardiff CityGillingham 1-0 Cardiff City | Emirates FA Cup Third Round |
| 38 | 12/1/2019 | 13-2 v Burton AlbionBurton Albion 2-3 Gillingham | Sky Bet League One |
| 39 | 19/1/2019 | 10-3 v WalsallGillingham 0-3 Walsall | Sky Bet League One |
| 40 | 26/1/2019 | 11-4 v Swansea CitySwansea City 4-1 Gillingham | Emirates FA Cup Fourth Round |
| 41 | 29/1/2019 | 10-0 v Accrington StanleyGillingham 0-0 Accrington Stanley | Sky Bet League One |
| 42 | 2/2/2019 | 11-1 v Coventry CityCoventry City 1-1 Gillingham | Sky Bet League One |
| 43 | 9/2/2019 | 11-4 v BarnsleyGillingham 1-4 Barnsley | Sky Bet League One |
| 44 | 16/2/2019 | 11-0 v Scunthorpe UnitedGillingham 1-0 Scunthorpe United | Sky Bet League One |
| 45 | 19/2/2019 | 12-4 v SunderlandSunderland 4-2 Gillingham | Sky Bet League One |
| 46 | 23/2/2019 | 11-0 v Wycombe WanderersWycombe Wanderers 0-1 Gillingham | Sky Bet League One |
| 47 | 2/3/2019 | 11-1 v Fleetwood TownFleetwood Town 1-1 Gillingham | Sky Bet League One |
| 48 | 9/3/2019 | 11-0 v Oxford UnitedGillingham 1-0 Oxford United | Sky Bet League One |
| 49 | 12/3/2019 | 10-1 v Bristol RoversGillingham 0-1 Bristol Rovers | Sky Bet League One |
| 50 | 16/3/2019 | 12-2 v Luton TownLuton Town 2-2 Gillingham | Sky Bet League One |
| 51 | 23/3/2019 | 14-2 v AFC WimbledonAFC Wimbledon 2-4 Gillingham | Sky Bet League One |
| 52 | 30/3/2019 | 11-1 v RochdaleGillingham 1-1 Rochdale | Sky Bet League One |
| 53 | 6/4/2019 | 10-2 v Peterborough UnitedPeterborough United 2-0 Gillingham | Sky Bet League One |
| 54 | 13/4/2019 | 10-2 v Shrewsbury TownGillingham 0-2 Shrewsbury Town | Sky Bet League One |
| 55 | 19/4/2019 | 13-1 v Plymouth ArgyleGillingham 3-1 Plymouth Argyle | Sky Bet League One |
| 56 | 22/4/2019 | 11-1 v Bradford CityBradford City 1-1 Gillingham | Sky Bet League One |
| 57 | 27/4/2019 | 10-2 v Charlton AthleticGillingham 0-2 Charlton Athletic | Sky Bet League One |
| 58 | 4/5/2019 | 13-0 v BlackpoolBlackpool 0-3 Gillingham | Sky Bet League One |
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