| 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 13 Aug 2019 | 2-2 v Newport CountyGillingham 2-2 Newport County | Carabao Cup First Round |
| 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 | Tue 17 Sep 2019 | 1-1 v Bristol RoversBristol Rovers 1-1 Gillingham | Sky Bet League One |
| 7 | Sat 5 Oct 2019 | 3-1 v Southend UnitedGillingham 3-1 Southend United | Sky Bet League One |
| 8 | Sat 12 Oct 2019 | 0-0 v PortsmouthPortsmouth 0-0 Gillingham | Sky Bet League One |
| 9 | Sat 19 Oct 2019 | 1-2 v Peterborough UnitedGillingham 1-2 Peterborough United | Sky Bet League One |
| 10 | Tue 22 Oct 2019 | 1-1 v Shrewsbury TownShrewsbury Town 1-1 Gillingham | Sky Bet League One |
| 11 | Sat 26 Oct 2019 | 1-0 v Accrington StanleyAccrington Stanley 0-1 Gillingham | Sky Bet League One |
| 12 | Sat 2 Nov 2019 | 0-3 v Rotherham UnitedGillingham 0-3 Rotherham United | Sky Bet League One |
| 13 | Tue 19 Nov 2019 | 1-0 v SunderlandGillingham 1-0 Sunderland | Emirates FA Cup First Round Replay |
| 14 | Sun 1 Dec 2019 | 3-0 v Doncaster RoversGillingham 3-0 Doncaster Rovers | Emirates FA Cup Second Round |
| 15 | Sun 5 Jan 2020 | 0-2 v West Ham UnitedGillingham 0-2 West Ham United | Emirates FA Cup Third Round |
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