| 1 | Tue 13 Aug 2019 | 2-2 v Crewe AlexandraMiddlesbrough 2-2 Crewe Alexandra | Carabao Cup First Round |
| 2 | Wed 23 Oct 2019 | 0-0 v Huddersfield TownHuddersfield Town 0-0 Middlesbrough | Sky Bet Championship |
| 3 | Sat 26 Oct 2019 | 0-0 v FulhamMiddlesbrough 0-0 Fulham | Sky Bet Championship |
| 4 | Sat 2 Nov 2019 | 0-2 v Derby CountyDerby County 2-0 Middlesbrough | Sky Bet Championship |
| 5 | Wed 27 Nov 2019 | 1-0 v BarnsleyMiddlesbrough 1-0 Barnsley | Sky Bet Championship |
| 6 | Sat 30 Nov 2019 | 0-4 v Leeds UnitedLeeds United 4-0 Middlesbrough | Sky Bet Championship |
| 7 | Sat 7 Dec 2019 | 1-0 v Charlton AthleticMiddlesbrough 1-0 Charlton Athletic | Sky Bet Championship |
| 8 | Tue 10 Dec 2019 | 1-1 v Nottingham ForestNottingham Forest 1-1 Middlesbrough | Sky Bet Championship |
| 9 | Sat 14 Dec 2019 | 1-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
| 10 | Fri 20 Dec 2019 | 2-1 v Stoke CityMiddlesbrough 2-1 Stoke City | Sky Bet Championship |
| 11 | Thu 26 Dec 2019 | 1-0 v Huddersfield TownMiddlesbrough 1-0 Huddersfield Town | Sky Bet Championship |
| 12 | Sun 29 Dec 2019 | 2-0 v West Bromwich AlbionWest Bromwich Albion 0-2 Middlesbrough | Sky Bet Championship |
| 13 | Wed 1 Jan 2020 | 2-0 v Preston North EndPreston North End 0-2 Middlesbrough | Sky Bet Championship |
| 14 | Sat 11 Jan 2020 | 2-2 v Derby CountyMiddlesbrough 2-2 Derby County | Sky Bet Championship |
| 15 | Fri 17 Jan 2020 | 0-1 v FulhamFulham 1-0 Middlesbrough | Sky Bet Championship |
| 16 | Tue 21 Jan 2020 | 1-1 v Birmingham CityMiddlesbrough 1-1 Birmingham City | Sky Bet Championship |
| 17 | Sat 1 Feb 2020 | 1-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 18 | Sat 8 Feb 2020 | 2-3 v BrentfordBrentford 3-2 Middlesbrough | Sky Bet Championship |
| 19 | Tue 11 Feb 2020 | 2-2 v Wigan AthleticWigan Athletic 2-2 Middlesbrough | Sky Bet Championship |
| 20 | Sat 15 Feb 2020 | 0-1 v Luton TownMiddlesbrough 0-1 Luton Town | Sky Bet Championship |
| 21 | Sat 22 Feb 2020 | 0-1 v BarnsleyBarnsley 1-0 Middlesbrough | Sky Bet Championship |
| 22 | Wed 26 Feb 2020 | 0-1 v Leeds UnitedMiddlesbrough 0-1 Leeds United | Sky Bet Championship |
| 23 | Mon 2 Mar 2020 | 2-2 v Nottingham ForestMiddlesbrough 2-2 Nottingham Forest | Sky Bet Championship |
| 24 | Tue 14 Jul 2020 | 422-1 v ReadingReading 1-2 Middlesbrough | Sky Bet Championship |
| 25 | Sat 18 Jul 2020 | 421-3 v Cardiff CityMiddlesbrough 1-3 Cardiff City | Sky Bet Championship |
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