| 1 | Tue 13 Aug 2019 | 282-2 v Crewe AlexandraMiddlesbrough 2-2 Crewe Alexandra | Carabao Cup First Round |
| 2 | Sat 14 Sep 2019 | 281-0 v ReadingMiddlesbrough 1-0 Reading | Sky Bet Championship |
| 3 | Sat 21 Sep 2019 | 280-1 v Cardiff CityCardiff City 1-0 Middlesbrough | Sky Bet Championship |
| 4 | Tue 1 Oct 2019 | 281-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 5 | Fri 4 Oct 2019 | 281-2 v Birmingham CityBirmingham City 2-1 Middlesbrough | Sky Bet Championship |
| 6 | Sat 19 Oct 2019 | 28 0-1 v West Bromwich AlbionMiddlesbrough 0-1 West Bromwich Albion | Sky Bet Championship |
| 7 | Wed 23 Oct 2019 | 280-0 v Huddersfield TownHuddersfield Town 0-0 Middlesbrough | Sky Bet Championship |
| 8 | Sat 26 Oct 2019 | 28 0-0 v FulhamMiddlesbrough 0-0 Fulham | Sky Bet Championship |
| 9 | Sat 2 Nov 2019 | 280-2 v Derby CountyDerby County 2-0 Middlesbrough | Sky Bet Championship |
| 10 | Sat 9 Nov 2019 | 282-2 v Queens Park RangersQueens Park Rangers 2-2 Middlesbrough | Sky Bet Championship |
| 11 | Sun 24 Nov 2019 | 282-2 v Hull CityMiddlesbrough 2-2 Hull City | Sky Bet Championship |
| 12 | Wed 27 Nov 2019 | 281-0 v BarnsleyMiddlesbrough 1-0 Barnsley | Sky Bet Championship |
| 13 | Sat 30 Nov 2019 | 280-4 v Leeds UnitedLeeds United 4-0 Middlesbrough | Sky Bet Championship |
| 14 | Sat 7 Dec 2019 | 281-0 v Charlton AthleticMiddlesbrough 1-0 Charlton Athletic | Sky Bet Championship |
| 15 | Tue 10 Dec 2019 | 281-1 v Nottingham ForestNottingham Forest 1-1 Middlesbrough | Sky Bet Championship |
| 16 | Sat 14 Dec 2019 | 281-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
| 17 | Fri 20 Dec 2019 | 28 2-1 v Stoke CityMiddlesbrough 2-1 Stoke City | Sky Bet Championship |
| 18 | Thu 26 Dec 2019 | 281-0 v Huddersfield TownMiddlesbrough 1-0 Huddersfield Town | Sky Bet Championship |
| 19 | Sun 29 Dec 2019 | 282-0 v West Bromwich AlbionWest Bromwich Albion 0-2 Middlesbrough | Sky Bet Championship |
| 20 | Wed 1 Jan 2020 | 282-0 v Preston North EndPreston North End 0-2 Middlesbrough | Sky Bet Championship |
| 21 | Sun 5 Jan 2020 | 281-1 v Tottenham HotspurMiddlesbrough 1-1 Tottenham Hotspur | Emirates FA Cup Third Round |
| 22 | Sat 11 Jan 2020 | 282-2 v Derby CountyMiddlesbrough 2-2 Derby County | Sky Bet Championship |
| 23 | Tue 14 Jan 2020 | 281-2 v Tottenham HotspurTottenham Hotspur 2-1 Middlesbrough | Emirates FA Cup Third Round Replay |
| 24 | Fri 17 Jan 2020 | 280-1 v FulhamFulham 1-0 Middlesbrough | Sky Bet Championship |
| 25 | Tue 21 Jan 2020 | 281-1 v Birmingham CityMiddlesbrough 1-1 Birmingham City | Sky Bet Championship |
| 26 | Sat 1 Feb 2020 | 281-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 27 | Sat 8 Feb 2020 | 28 2-3 v BrentfordBrentford 3-2 Middlesbrough | Sky Bet Championship |
| 28 | Tue 11 Feb 2020 | 28 2-2 v Wigan AthleticWigan Athletic 2-2 Middlesbrough | Sky Bet Championship |
| 29 | Wed 26 Feb 2020 | 280-1 v Leeds UnitedMiddlesbrough 0-1 Leeds United | Sky Bet Championship |
| 30 | Mon 2 Mar 2020 | 282-2 v Nottingham ForestMiddlesbrough 2-2 Nottingham Forest | Sky Bet Championship |
| 31 | Sat 7 Mar 2020 | 281-0 v Charlton AthleticCharlton Athletic 0-1 Middlesbrough | Sky Bet Championship |
| 32 | Sat 27 Jun 2020 | 72-0 v Stoke CityStoke City 0-2 Middlesbrough | Sky Bet Championship |
| 33 | Thu 2 Jul 2020 | 7 1-2 v Hull CityHull City 2-1 Middlesbrough | Sky Bet Championship |
| 34 | Sun 5 Jul 2020 | 70-1 v Queens Park RangersMiddlesbrough 0-1 Queens Park Rangers | Sky Bet Championship |
| 35 | Wed 8 Jul 2020 | 72-0 v MillwallMillwall 0-2 Middlesbrough | Sky Bet Championship |
| 36 | Sat 11 Jul 2020 | 71-3 v Bristol CityMiddlesbrough 1-3 Bristol City | Sky Bet Championship |
| 37 | Tue 14 Jul 2020 | 72-1 v ReadingReading 1-2 Middlesbrough | Sky Bet Championship |
| 38 | Sat 18 Jul 2020 | 71-3 v Cardiff CityMiddlesbrough 1-3 Cardiff City | Sky Bet Championship |
| 39 | Wed 22 Jul 2020 | 72-1 v Sheffield WednesdaySheffield Wednesday 1-2 Middlesbrough | Sky Bet Championship |
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