| 1 | Sat 10 Aug 2019 | 1-1 v SunderlandIpswich Town 1-1 Sunderland | Sky Bet League One |
| 2 | Tue 13 Aug 2019 | 1-3 v Luton TownLuton Town 3-1 Ipswich Town | Carabao Cup First Round |
| 3 | Tue 8 Oct 2019 | 4-0 v GillinghamIpswich Town 4-0 Gillingham | Leasing.com Trophy Southern Group A |
| 4 | Sat 11 Jan 2020 | 0-0 v Peterborough UnitedPeterborough United 0-0 Gillingham | Sky Bet League One |
| 5 | Sat 18 Jan 2020 | 1-1 v Oxford UnitedGillingham 1-1 Oxford United | Sky Bet League One |
| 6 | Wed 29 Jan 2020 | 2-0 v Shrewsbury TownGillingham 2-0 Shrewsbury Town | Sky Bet League One |
| 7 | Sat 8 Feb 2020 | 0-0 v Burton AlbionBurton Albion 0-0 Gillingham | Sky Bet League One |
| 8 | Tue 11 Feb 2020 | 3-2 v BlackpoolBlackpool 2-3 Gillingham | Sky Bet League One |
| 9 | Sat 15 Feb 2020 | 2-1 v Doncaster RoversGillingham 2-1 Doncaster Rovers | Sky Bet League One |
| 10 | Tue 18 Feb 2020 | 1-0 v Southend UnitedSouthend United 0-1 Gillingham | Sky Bet League One |
| 11 | Sat 22 Feb 2020 | 0-0 v Lincoln CityLincoln City 0-0 Gillingham | Sky Bet League One |
| 12 | Sat 7 Mar 2020 | 2-2 v SunderlandSunderland 2-2 Gillingham | Sky Bet League One |
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