| 1 | Sat 10 Aug 2019 | 1-2 v Burton AlbionGillingham 1-2 Burton Albion | Sky Bet League One |
| 2 | Tue 13 Aug 2019 | 2-2 v Newport CountyGillingham 2-2 Newport County | Carabao Cup First Round |
| 3 | Tue 20 Aug 2019 | 2-2 v BlackpoolGillingham 2-2 Blackpool | Sky Bet League One |
| 4 | Sat 31 Aug 2019 | 5-0 v Bolton WanderersGillingham 5-0 Bolton Wanderers | 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 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 2 Nov 2019 | 0-3 v Rotherham UnitedGillingham 0-3 Rotherham United | Sky Bet League One |
| 13 | Sat 23 Nov 2019 | 0-1 v AFC WimbledonAFC Wimbledon 1-0 Gillingham | Sky Bet League One |
| 14 | Sat 7 Dec 2019 | 1-0 v SunderlandGillingham 1-0 Sunderland | Sky Bet League One |
| 15 | Sat 14 Dec 2019 | 1-1 v Fleetwood TownFleetwood Town 1-1 Gillingham | Sky Bet League One |
| 16 | Sat 21 Dec 2019 | 3-1 v Milton Keynes DonsGillingham 3-1 Milton Keynes Dons | Sky Bet League One |
| 17 | Sun 29 Dec 2019 | 1-0 v RochdaleGillingham 1-0 Rochdale | Sky Bet League One |
| 18 | Wed 1 Jan 2020 | 1-1 v PortsmouthGillingham 1-1 Portsmouth | Sky Bet League One |
| 19 | Sun 5 Jan 2020 | 0-2 v West Ham UnitedGillingham 0-2 West Ham United | Emirates FA Cup Third Round |
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