| 1 | Tue 13 Aug 2019 | 2-2 v AFC WimbledonAFC Wimbledon 2-2 Milton Keynes Dons | Carabao Cup First Round |
| 2 | Sat 17 Aug 2019 | 2-3 v Wycombe WanderersWycombe Wanderers 3-2 Milton Keynes Dons | Sky Bet League One |
| 3 | Tue 20 Aug 2019 | 2-1 v Lincoln CityMilton Keynes Dons 2-1 Lincoln City | Sky Bet League One |
| 4 | Tue 27 Aug 2019 | 4-1 v Southend UnitedSouthend United 1-4 Milton Keynes Dons | Carabao Cup Second Round |
| 5 | Sat 14 Sep 2019 | 3-0 v BlackpoolBlackpool 0-3 Milton Keynes Dons | Sky Bet League One |
| 6 | Tue 17 Sep 2019 | 0-1 v Ipswich TownMilton Keynes Dons 0-1 Ipswich Town | Sky Bet League One |
| 7 | Sat 21 Sep 2019 | 0-1 v Southend UnitedMilton Keynes Dons 0-1 Southend United | Sky Bet League One |
| 8 | Wed 25 Sep 2019 | 0-2 v LiverpoolMilton Keynes Dons 0-2 Liverpool | Carabao Cup Third Round |
| 9 | Sat 28 Sep 2019 | 1-2 v SunderlandSunderland 2-1 Milton Keynes Dons | Sky Bet League One |
| 10 | Sat 5 Oct 2019 | 0-3 v Burton AlbionMilton Keynes Dons 0-3 Burton Albion | Sky Bet League One |
| 11 | Sat 26 Oct 2019 | 0-1 v Fleetwood TownFleetwood Town 1-0 Milton Keynes Dons | Sky Bet League One |
| 12 | Sat 2 Nov 2019 | 1-3 v Tranmere RoversMilton Keynes Dons 1-3 Tranmere Rovers | Sky Bet League One |
| 13 | Sat 9 Nov 2019 | 0-1 v Port ValeMilton Keynes Dons 0-1 Port Vale | Emirates FA Cup First Round |
| 14 | Sat 23 Nov 2019 | 2-3 v Rotherham UnitedMilton Keynes Dons 2-3 Rotherham United | Sky Bet League One |
| 15 | Sat 14 Dec 2019 | 1-0 v Oxford UnitedMilton Keynes Dons 1-0 Oxford United | Sky Bet League One |
| 16 | Sat 21 Dec 2019 | 1-3 v GillinghamGillingham 3-1 Milton Keynes Dons | Sky Bet League One |
| 17 | Thu 26 Dec 2019 | 2-2 v Southend UnitedSouthend United 2-2 Milton Keynes Dons | Sky Bet League One |
| 18 | Tue 7 Jan 2020 | 0-3 v Newport CountyNewport County 3-0 Milton Keynes Dons | Leasing.com Trophy Round of 16 |
| 19 | Sat 8 Feb 2020 | 1-1 v Shrewsbury TownShrewsbury Town 1-1 Milton Keynes Dons | Sky Bet League One |
| 20 | Tue 11 Feb 2020 | 1-1 v Lincoln CityLincoln City 1-1 Milton Keynes Dons | Sky Bet League One |
| 21 | Sat 22 Feb 2020 | 1-0 v Bolton WanderersMilton Keynes Dons 1-0 Bolton Wanderers | Sky Bet League One |
| 22 | Tue 25 Feb 2020 | 1-3 v PortsmouthPortsmouth 3-1 Milton Keynes Dons | Sky Bet League One |
| 23 | Sat 29 Feb 2020 | 1-1 v Rotherham UnitedRotherham United 1-1 Milton Keynes Dons | Sky Bet League One |
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