| 1 | Fri 2 Aug 2019 | 83-3 v Luton TownLuton Town 3-3 Middlesbrough | Sky Bet Championship |
| 2 | Sat 10 Aug 2019 | 80-1 v BrentfordMiddlesbrough 0-1 Brentford | Sky Bet Championship |
| 3 | Tue 13 Aug 2019 | 82-2 v Crewe AlexandraMiddlesbrough 2-2 Crewe Alexandra | Carabao Cup First Round |
| 4 | Tue 20 Aug 2019 | 81-0 v Wigan AthleticMiddlesbrough 1-0 Wigan Athletic | Sky Bet Championship |
| 5 | Sat 24 Aug 2019 | 81-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 6 | Sat 31 Aug 2019 | 82-2 v Bristol CityBristol City 2-2 Middlesbrough | Sky Bet Championship |
| 7 | Sat 14 Sep 2019 | 81-0 v ReadingMiddlesbrough 1-0 Reading | Sky Bet Championship |
| 8 | Sat 21 Sep 2019 | 80-1 v Cardiff CityCardiff City 1-0 Middlesbrough | Sky Bet Championship |
| 9 | Sat 28 Sep 2019 | 81-4 v Sheffield WednesdayMiddlesbrough 1-4 Sheffield Wednesday | Sky Bet Championship |
| 10 | Tue 1 Oct 2019 | 8 1-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 11 | Fri 4 Oct 2019 | 81-2 v Birmingham CityBirmingham City 2-1 Middlesbrough | Sky Bet Championship |
| 12 | Wed 23 Oct 2019 | 80-0 v Huddersfield TownHuddersfield Town 0-0 Middlesbrough | Sky Bet Championship |
| 13 | Sat 9 Nov 2019 | 82-2 v Queens Park RangersQueens Park Rangers 2-2 Middlesbrough | Sky Bet Championship |
| 14 | Sun 24 Nov 2019 | 8 2-2 v Hull CityMiddlesbrough 2-2 Hull City | Sky Bet Championship |
| 15 | Wed 27 Nov 2019 | 81-0 v BarnsleyMiddlesbrough 1-0 Barnsley | Sky Bet Championship |
| 16 | Sat 7 Dec 2019 | 81-0 v Charlton AthleticMiddlesbrough 1-0 Charlton Athletic | Sky Bet Championship |
| 17 | Tue 10 Dec 2019 | 81-1 v Nottingham ForestNottingham Forest 1-1 Middlesbrough | Sky Bet Championship |
| 18 | Sat 14 Dec 2019 | 81-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
| 19 | Fri 20 Dec 2019 | 82-1 v Stoke CityMiddlesbrough 2-1 Stoke City | Sky Bet Championship |
| 20 | Sun 29 Dec 2019 | 82-0 v West Bromwich AlbionWest Bromwich Albion 0-2 Middlesbrough | Sky Bet Championship |
| 21 | Wed 1 Jan 2020 | 8 2-0 v Preston North EndPreston North End 0-2 Middlesbrough | Sky Bet Championship |
| 22 | Sun 5 Jan 2020 | 81-1 v Tottenham HotspurMiddlesbrough 1-1 Tottenham Hotspur | Emirates FA Cup Third Round |
| 23 | Tue 14 Jan 2020 | 81-2 v Tottenham HotspurTottenham Hotspur 2-1 Middlesbrough | Emirates FA Cup Third Round Replay |
| 24 | Fri 17 Jan 2020 | 80-1 v FulhamFulham 1-0 Middlesbrough | Sky Bet Championship |
| 25 | Wed 26 Feb 2020 | 8 0-1 v Leeds UnitedMiddlesbrough 0-1 Leeds United | Sky Bet Championship |
| 26 | Mon 2 Mar 2020 | 82-2 v Nottingham ForestMiddlesbrough 2-2 Nottingham Forest | Sky Bet Championship |
| 27 | Sat 7 Mar 2020 | 81-0 v Charlton AthleticCharlton Athletic 0-1 Middlesbrough | Sky Bet Championship |
| 28 | Sat 20 Jun 2020 | 80-3 v Swansea CityMiddlesbrough 0-3 Swansea City | Sky Bet Championship |
| 29 | Wed 8 Jul 2020 | 82-0 v MillwallMillwall 0-2 Middlesbrough | Sky Bet Championship |
| 30 | Sat 11 Jul 2020 | 81-3 v Bristol CityMiddlesbrough 1-3 Bristol City | Sky Bet Championship |
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