| 1 | Sat 3 Aug 2019 | 1-2 v Rotherham UnitedAFC Wimbledon 1-2 Rotherham United | Sky Bet League One |
| 2 | Sat 10 Aug 2019 | 1-2 v Fleetwood TownFleetwood Town 2-1 AFC Wimbledon | Sky Bet League One |
| 3 | Tue 13 Aug 2019 | 2-2 v Milton Keynes DonsAFC Wimbledon 2-2 Milton Keynes Dons | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 1-1 v Accrington StanleyAFC Wimbledon 1-1 Accrington Stanley | Sky Bet League One |
| 5 | Tue 20 Aug 2019 | 1-2 v Ipswich TownIpswich Town 2-1 AFC Wimbledon | Sky Bet League One |
| 6 | Sat 24 Aug 2019 | 1-3 v SunderlandSunderland 3-1 AFC Wimbledon | Sky Bet League One |
| 7 | Sat 31 Aug 2019 | 0-0 v Wycombe WanderersAFC Wimbledon 0-0 Wycombe Wanderers | Sky Bet League One |
| 8 | Tue 17 Sep 2019 | 1-2 v Coventry CityCoventry City 2-1 AFC Wimbledon | Sky Bet League One |
| 9 | Sat 21 Sep 2019 | 1-3 v Bristol RoversAFC Wimbledon 1-3 Bristol Rovers | Sky Bet League One |
| 10 | Sat 28 Sep 2019 | 2-3 v Peterborough UnitedPeterborough United 3-2 AFC Wimbledon | Sky Bet League One |
| 11 | Sat 5 Oct 2019 | 3-2 v RochdaleAFC Wimbledon 3-2 Rochdale | Sky Bet League One |
| 12 | Tue 8 Oct 2019 | 3-0 v Leyton OrientAFC Wimbledon 3-0 Leyton Orient | Leasing.com Trophy Southern Group C |
| 13 | Sat 9 Nov 2019 | 1-1 v Doncaster RoversAFC Wimbledon 1-1 Doncaster Rovers | Emirates FA Cup First Round |
| 14 | Sat 16 Nov 2019 | 0-2 v BlackpoolBlackpool 2-0 AFC Wimbledon | Sky Bet League One |
| 15 | Tue 19 Nov 2019 | 0-2 v Doncaster RoversDoncaster Rovers 2-0 AFC Wimbledon | Emirates FA Cup First Round Replay |
| 16 | Sat 23 Nov 2019 | 1-0 v GillinghamAFC Wimbledon 1-0 Gillingham | Sky Bet League One |
| 17 | Sat 7 Dec 2019 | 2-2 v Bolton WanderersBolton Wanderers 2-2 AFC Wimbledon | Sky Bet League One |
| 18 | Sat 14 Dec 2019 | 2-1 v Doncaster RoversAFC Wimbledon 2-1 Doncaster Rovers | Sky Bet League One |
| 19 | Sat 21 Dec 2019 | 0-1 v Tranmere RoversTranmere Rovers 1-0 AFC Wimbledon | Sky Bet League One |
| 20 | Thu 26 Dec 2019 | 2-1 v Bristol RoversBristol Rovers 1-2 AFC Wimbledon | Sky Bet League One |
| 21 | Sun 29 Dec 2019 | 1-2 v Oxford UnitedAFC Wimbledon 1-2 Oxford United | Sky Bet League One |
| 22 | Wed 1 Jan 2020 | 1-1 v Southend UnitedAFC Wimbledon 1-1 Southend United | Sky Bet League One |
| 23 | Sat 11 Jan 2020 | 1-2 v PortsmouthPortsmouth 2-1 AFC Wimbledon | Sky Bet League One |
| 24 | Sat 18 Jan 2020 | 1-0 v Peterborough UnitedAFC Wimbledon 1-0 Peterborough United | Sky Bet League One |
| 25 | Sat 1 Feb 2020 | 1-2 v Accrington StanleyAccrington Stanley 2-1 AFC Wimbledon | Sky Bet League One |
| 26 | Sat 8 Feb 2020 | 1-2 v Fleetwood TownAFC Wimbledon 1-2 Fleetwood Town | Sky Bet League One |
| 27 | Tue 11 Feb 2020 | 0-0 v Ipswich TownAFC Wimbledon 0-0 Ipswich Town | Sky Bet League One |
| 28 | Sat 15 Feb 2020 | 2-2 v Rotherham UnitedRotherham United 2-2 AFC Wimbledon | Sky Bet League One |
| 29 | Sat 22 Feb 2020 | 0-0 v BlackpoolAFC Wimbledon 0-0 Blackpool | Sky Bet League One |
| 30 | Sat 29 Feb 2020 | 2-1 v GillinghamGillingham 1-2 AFC Wimbledon | Sky Bet League One |
| 31 | Sat 7 Mar 2020 | 0-0 v Bolton WanderersAFC Wimbledon 0-0 Bolton Wanderers | Sky Bet League One |
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