| 1 | Tue 20 Aug 2019 | 3-2 v Accrington StanleyAccrington Stanley 2-3 Shrewsbury Town | Sky Bet League One |
| 2 | Sat 24 Aug 2019 | 0-0 v Burton AlbionShrewsbury Town 0-0 Burton Albion | Sky Bet League One |
| 3 | Sat 31 Aug 2019 | 0-3 v Ipswich TownIpswich Town 3-0 Shrewsbury Town | Sky Bet League One |
| 4 | Tue 3 Sep 2019 | 1-2 v Port ValePort Vale 2-1 Shrewsbury Town | Leasing.com Trophy Northern Group D |
| 5 | Sat 5 Oct 2019 | 1-0 v Tranmere RoversTranmere Rovers 0-1 Shrewsbury Town | Sky Bet League One |
| 6 | Fri 18 Oct 2019 | 0-0 v Lincoln CityLincoln City 0-0 Shrewsbury Town | Sky Bet League One |
| 7 | Sat 26 Oct 2019 | 1-0 v SunderlandShrewsbury Town 1-0 Sunderland | Sky Bet League One |
| 8 | Sat 2 Nov 2019 | 0-1 v Wycombe WanderersWycombe Wanderers 1-0 Shrewsbury Town | Sky Bet League One |
| 9 | Wed 13 Nov 2019 | 3-1 v Macclesfield TownShrewsbury Town 3-1 Macclesfield Town | Leasing.com Trophy Northern Group D |
| 10 | Tue 19 Nov 2019 | 1-0 v Bradford CityBradford City 0-1 Shrewsbury Town | Emirates FA Cup First Round Replay |
| 11 | Sat 23 Nov 2019 | 3-4 v Bristol RoversShrewsbury Town 3-4 Bristol Rovers | Sky Bet League One |
| 12 | Tue 28 Jan 2020 | 2-1 v RochdaleMilton Keynes Dons 2-1 Rochdale | Sky Bet League One |
| 13 | Sat 1 Feb 2020 | 2-0 v Wycombe WanderersMilton Keynes Dons 2-0 Wycombe Wanderers | Sky Bet League One |
| 14 | Sat 8 Feb 2020 | 1-1 v Shrewsbury TownShrewsbury Town 1-1 Milton Keynes Dons | Sky Bet League One |
| 15 | Tue 11 Feb 2020 | 1-1 v Lincoln CityLincoln City 1-1 Milton Keynes Dons | Sky Bet League One |
| 16 | Sat 22 Feb 2020 | 1-0 v Bolton WanderersMilton Keynes Dons 1-0 Bolton Wanderers | Sky Bet League One |
| 17 | Tue 25 Feb 2020 | 1-3 v PortsmouthPortsmouth 3-1 Milton Keynes Dons | Sky Bet League One |
| 18 | Sat 29 Feb 2020 | 1-1 v Rotherham UnitedRotherham United 1-1 Milton Keynes Dons | Sky Bet League One |
| 19 | Sat 7 Mar 2020 | 0-1 v Doncaster RoversMilton Keynes Dons 0-1 Doncaster Rovers | Sky Bet League One |
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