| 1 | Sat 10 Aug 2019 | 0-1 v BrentfordMiddlesbrough 0-1 Brentford | Sky Bet Championship |
| 2 | Tue 13 Aug 2019 | 2-2 v Crewe AlexandraMiddlesbrough 2-2 Crewe Alexandra | Carabao Cup First Round |
| 3 | Tue 20 Aug 2019 | 1-0 v Wigan AthleticMiddlesbrough 1-0 Wigan Athletic | Sky Bet Championship |
| 4 | Sat 24 Aug 2019 | 1-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 5 | Sat 21 Sep 2019 | 0-1 v Cardiff CityCardiff City 1-0 Middlesbrough | Sky Bet Championship |
| 6 | Sat 28 Sep 2019 | 1-4 v Sheffield WednesdayMiddlesbrough 1-4 Sheffield Wednesday | Sky Bet Championship |
| 7 | Tue 1 Oct 2019 | 1-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 8 | Fri 4 Oct 2019 | 1-2 v Birmingham CityBirmingham City 2-1 Middlesbrough | Sky Bet Championship |
| 9 | Sat 19 Oct 2019 | 0-1 v West Bromwich AlbionMiddlesbrough 0-1 West Bromwich Albion | Sky Bet Championship |
| 10 | Sat 26 Oct 2019 | 0-0 v FulhamMiddlesbrough 0-0 Fulham | Sky Bet Championship |
| 11 | Sat 2 Nov 2019 | 0-2 v Derby CountyDerby County 2-0 Middlesbrough | Sky Bet Championship |
| 12 | Sat 14 Dec 2019 | 1-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
| 13 | Sat 11 Jan 2020 | 1-3 v Rotherham UnitedOxford United 1-3 Rotherham United | Sky Bet League One |
| 14 | Tue 14 Jan 2020 | 0-0 v Ipswich TownOxford United 0-0 Ipswich Town | Sky Bet League One |
| 15 | Sat 18 Jan 2020 | 1-1 v GillinghamGillingham 1-1 Oxford United | Sky Bet League One |
| 16 | Sat 25 Jan 2020 | 0-0 v Newcastle UnitedNewcastle United 0-0 Oxford United | Emirates FA Cup Fourth Round |
| 17 | Sat 1 Feb 2020 | 2-1 v BlackpoolOxford United 2-1 Blackpool | Sky Bet League One |
| 18 | Tue 4 Feb 2020 | 2-3 v Newcastle UnitedOxford United 2-3 Newcastle United | Emirates FA Cup Fourth Round Replay |
| 19 | Sat 8 Feb 2020 | 0-4 v Peterborough UnitedPeterborough United 4-0 Oxford United | Sky Bet League One |
| 20 | Sat 15 Feb 2020 | 0-1 v SunderlandOxford United 0-1 Sunderland | Sky Bet League One |
| 21 | Tue 18 Feb 2020 | 5-0 v AFC WimbledonOxford United 5-0 AFC Wimbledon | Sky Bet League One |
| 22 | Sat 22 Feb 2020 | 1-0 v Ipswich TownIpswich Town 0-1 Oxford United | Sky Bet League One |
| 23 | Tue 25 Feb 2020 | 3-0 v Accrington StanleyOxford United 3-0 Accrington Stanley | Sky Bet League One |
| 24 | Sat 29 Feb 2020 | 2-1 v Southend UnitedOxford United 2-1 Southend United | Sky Bet League One |
| 25 | Sat 7 Mar 2020 | 3-2 v Shrewsbury TownShrewsbury Town 2-3 Oxford United | Sky Bet League One |
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