| 1 | Sat 7 Dec 2019 | 1-0 v Charlton AthleticMiddlesbrough 1-0 Charlton Athletic | Sky Bet Championship |
| 2 | Tue 10 Dec 2019 | 1-1 v Nottingham ForestNottingham Forest 1-1 Middlesbrough | Sky Bet Championship |
| 3 | Fri 20 Dec 2019 | 2-1 v Stoke CityMiddlesbrough 2-1 Stoke City | Sky Bet Championship |
| 4 | Thu 26 Dec 2019 | 1-0 v Huddersfield TownMiddlesbrough 1-0 Huddersfield Town | Sky Bet Championship |
| 5 | Sun 29 Dec 2019 | 2-0 v West Bromwich AlbionWest Bromwich Albion 0-2 Middlesbrough | Sky Bet Championship |
| 6 | Wed 1 Jan 2020 | 2-0 v Preston North EndPreston North End 0-2 Middlesbrough | Sky Bet Championship |
| 7 | Sun 5 Jan 2020 | 1-1 v Tottenham HotspurMiddlesbrough 1-1 Tottenham Hotspur | Emirates FA Cup Third Round |
| 8 | Sat 11 Jan 2020 | 2-2 v Derby CountyMiddlesbrough 2-2 Derby County | Sky Bet Championship |
| 9 | Tue 14 Jan 2020 | 1-2 v Tottenham HotspurTottenham Hotspur 2-1 Middlesbrough | Emirates FA Cup Third Round Replay |
| 10 | Fri 17 Jan 2020 | 0-1 v FulhamFulham 1-0 Middlesbrough | Sky Bet Championship |
| 11 | Tue 21 Jan 2020 | 1-1 v Birmingham CityMiddlesbrough 1-1 Birmingham City | Sky Bet Championship |
| 12 | Sat 1 Feb 2020 | 1-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 13 | Tue 11 Feb 2020 | 2-2 v Wigan AthleticWigan Athletic 2-2 Middlesbrough | Sky Bet Championship |
| 14 | Sat 15 Feb 2020 | 0-1 v Luton TownMiddlesbrough 0-1 Luton Town | Sky Bet Championship |
| 15 | Mon 2 Mar 2020 | 2-2 v Nottingham ForestMiddlesbrough 2-2 Nottingham Forest | Sky Bet Championship |
| 16 | Sat 7 Mar 2020 | 1-0 v Charlton AthleticCharlton Athletic 0-1 Middlesbrough | Sky Bet Championship |
| 17 | Sat 20 Jun 2020 | 290-3 v Swansea CityMiddlesbrough 0-3 Swansea City | Sky Bet Championship |
| 18 | Sat 27 Jun 2020 | 292-0 v Stoke CityStoke City 0-2 Middlesbrough | Sky Bet Championship |
| 19 | Thu 2 Jul 2020 | 291-2 v Hull CityHull City 2-1 Middlesbrough | Sky Bet Championship |
| 20 | Wed 8 Jul 2020 | 292-0 v MillwallMillwall 0-2 Middlesbrough | Sky Bet Championship |
| 21 | Sat 11 Jul 2020 | 291-3 v Bristol CityMiddlesbrough 1-3 Bristol City | Sky Bet Championship |
| 22 | Tue 14 Jul 2020 | 292-1 v ReadingReading 1-2 Middlesbrough | Sky Bet Championship |
| 23 | Sat 18 Jul 2020 | 291-3 v Cardiff CityMiddlesbrough 1-3 Cardiff City | Sky Bet Championship |
| 24 | Wed 22 Jul 2020 | 292-1 v Sheffield WednesdaySheffield Wednesday 1-2 Middlesbrough | Sky Bet Championship |
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