| 1 | Sat 3 Aug 2019 | 1-1 v Doncaster RoversDoncaster Rovers 1-1 Gillingham | Sky Bet League One |
| 2 | Sat 10 Aug 2019 | 1-2 v Burton AlbionGillingham 1-2 Burton Albion | Sky Bet League One |
| 3 | Tue 20 Aug 2019 | 2-2 v BlackpoolGillingham 2-2 Blackpool | Sky Bet League One |
| 4 | Sat 24 Aug 2019 | 0-1 v Coventry CityCoventry City 1-0 Gillingham | Sky Bet League One |
| 5 | Sat 14 Sep 2019 | 2-0 v Wycombe WanderersGillingham 2-0 Wycombe Wanderers | Sky Bet League One |
| 6 | Sat 21 Sep 2019 | 0-1 v Ipswich TownGillingham 0-1 Ipswich Town | Sky Bet League One |
| 7 | Sat 28 Sep 2019 | 0-3 v Oxford UnitedOxford United 3-0 Gillingham | Sky Bet League One |
| 8 | Sat 5 Oct 2019 | 3-1 v Southend UnitedGillingham 3-1 Southend United | Sky Bet League One |
| 9 | Sat 12 Oct 2019 | 0-0 v PortsmouthPortsmouth 0-0 Gillingham | Sky Bet League One |
| 10 | Sat 19 Oct 2019 | 1-2 v Peterborough UnitedGillingham 1-2 Peterborough United | Sky Bet League One |
| 11 | Tue 22 Oct 2019 | 1-1 v Shrewsbury TownShrewsbury Town 1-1 Gillingham | Sky Bet League One |
| 12 | Sat 26 Oct 2019 | 1-0 v Accrington StanleyAccrington Stanley 0-1 Gillingham | Sky Bet League One |
| 13 | Sat 2 Nov 2019 | 0-3 v Rotherham UnitedGillingham 0-3 Rotherham United | Sky Bet League One |
| 14 | Sat 9 Nov 2019 | 1-1 v SunderlandSunderland 1-1 Gillingham | Emirates FA Cup First Round |
| 15 | Sat 16 Nov 2019 | 1-0 v Lincoln CityGillingham 1-0 Lincoln City | Sky Bet League One |
| 16 | Tue 19 Nov 2019 | 1-0 v SunderlandGillingham 1-0 Sunderland | Emirates FA Cup First Round Replay |
| 17 | Sat 23 Nov 2019 | 0-1 v AFC WimbledonAFC Wimbledon 1-0 Gillingham | Sky Bet League One |
| 18 | Sat 14 Dec 2019 | 1-1 v Fleetwood TownFleetwood Town 1-1 Gillingham | Sky Bet League One |
| 19 | Sat 21 Dec 2019 | 3-1 v Milton Keynes DonsGillingham 3-1 Milton Keynes Dons | Sky Bet League One |
| 20 | Thu 26 Dec 2019 | 0-0 v Ipswich TownIpswich Town 0-0 Gillingham | Sky Bet League One |
| 21 | Sun 29 Dec 2019 | 1-0 v RochdaleGillingham 1-0 Rochdale | Sky Bet League One |
| 22 | Wed 1 Jan 2020 | 1-1 v PortsmouthGillingham 1-1 Portsmouth | Sky Bet League One |
| 23 | Sun 5 Jan 2020 | 0-2 v West Ham UnitedGillingham 0-2 West Ham United | Emirates FA Cup Third Round |
| 24 | Sat 11 Jan 2020 | 0-0 v Peterborough UnitedPeterborough United 0-0 Gillingham | Sky Bet League One |
| 25 | Sat 18 Jan 2020 | 1-1 v Oxford UnitedGillingham 1-1 Oxford United | Sky Bet League One |
| 26 | Wed 29 Jan 2020 | 2-0 v Shrewsbury TownGillingham 2-0 Shrewsbury Town | Sky Bet League One |
| 27 | Tue 11 Feb 2020 | 3-2 v BlackpoolBlackpool 2-3 Gillingham | Sky Bet League One |
| 28 | Sat 15 Feb 2020 | 2-1 v Doncaster RoversGillingham 2-1 Doncaster Rovers | Sky Bet League One |
| 29 | Sat 22 Feb 2020 | 0-0 v Lincoln CityLincoln City 0-0 Gillingham | Sky Bet League One |
| 30 | Sat 29 Feb 2020 | 1-2 v AFC WimbledonGillingham 1-2 AFC Wimbledon | Sky Bet League One |
| 31 | Sat 7 Mar 2020 | 2-2 v SunderlandSunderland 2-2 Gillingham | Sky Bet League One |
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