| 1 | 3/8/2019 | 1-1 v Doncaster RoversDoncaster Rovers 1-1 Gillingham | Sky Bet League One |
| 2 | 10/8/2019 | 1-2 v Burton AlbionGillingham 1-2 Burton Albion | Sky Bet League One |
| 3 | 13/8/2019 | 2-2 v Newport CountyGillingham 2-2 Newport County | Carabao Cup First Round |
| 4 | 20/8/2019 | 2-2 v BlackpoolGillingham 2-2 Blackpool | Sky Bet League One |
| 5 | 24/8/2019 | 0-1 v Coventry CityCoventry City 1-0 Gillingham | Sky Bet League One |
| 6 | 31/8/2019 | 5-0 v Bolton WanderersGillingham 5-0 Bolton Wanderers | Sky Bet League One |
| 7 | 14/9/2019 | 2-0 v Wycombe WanderersGillingham 2-0 Wycombe Wanderers | Sky Bet League One |
| 8 | 17/9/2019 | 1-1 v Bristol RoversBristol Rovers 1-1 Gillingham | Sky Bet League One |
| 9 | 28/9/2019 | 0-3 v Oxford UnitedOxford United 3-0 Gillingham | Sky Bet League One |
| 10 | 5/10/2019 | 3-1 v Southend UnitedGillingham 3-1 Southend United | Sky Bet League One |
| 11 | 12/10/2019 | 0-0 v PortsmouthPortsmouth 0-0 Gillingham | Sky Bet League One |
| 12 | 19/10/2019 | 1-2 v Peterborough UnitedGillingham 1-2 Peterborough United | Sky Bet League One |
| 13 | 22/10/2019 | 1-1 v Shrewsbury TownShrewsbury Town 1-1 Gillingham | Sky Bet League One |
| 14 | 26/10/2019 | 1-0 v Accrington StanleyAccrington Stanley 0-1 Gillingham | Sky Bet League One |
| 15 | 2/11/2019 | 0-3 v Rotherham UnitedGillingham 0-3 Rotherham United | Sky Bet League One |
| 16 | 9/11/2019 | 1-1 v SunderlandSunderland 1-1 Gillingham | Emirates FA Cup First Round |
| 17 | 16/11/2019 | 1-0 v Lincoln CityGillingham 1-0 Lincoln City | Sky Bet League One |
| 18 | 19/11/2019 | 1-0 v SunderlandGillingham 1-0 Sunderland | Emirates FA Cup First Round Replay |
| 19 | 23/11/2019 | 0-1 v AFC WimbledonAFC Wimbledon 1-0 Gillingham | Sky Bet League One |
| 20 | 1/12/2019 | 3-0 v Doncaster RoversGillingham 3-0 Doncaster Rovers | Emirates FA Cup Second Round |
| 21 | 7/12/2019 | 1-0 v SunderlandGillingham 1-0 Sunderland | Sky Bet League One |
