| 1 | Fri 2 Aug 2019 | 93-3 v Luton TownLuton Town 3-3 Middlesbrough | Sky Bet Championship |
| 2 | Sat 10 Aug 2019 | 90-1 v BrentfordMiddlesbrough 0-1 Brentford | Sky Bet Championship |
| 3 | Tue 13 Aug 2019 | 92-2 v Crewe AlexandraMiddlesbrough 2-2 Crewe Alexandra | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 90-1 v Blackburn RoversBlackburn Rovers 1-0 Middlesbrough | Sky Bet Championship |
| 5 | Tue 20 Aug 2019 | 91-0 v Wigan AthleticMiddlesbrough 1-0 Wigan Athletic | Sky Bet Championship |
| 6 | Sat 24 Aug 2019 | 91-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 7 | Sat 31 Aug 2019 | 92-2 v Bristol CityBristol City 2-2 Middlesbrough | Sky Bet Championship |
| 8 | Sat 14 Sep 2019 | 91-0 v ReadingMiddlesbrough 1-0 Reading | Sky Bet Championship |
| 9 | Sat 21 Sep 2019 | 90-1 v Cardiff CityCardiff City 1-0 Middlesbrough | Sky Bet Championship |
| 10 | Sat 28 Sep 2019 | 91-4 v Sheffield WednesdayMiddlesbrough 1-4 Sheffield Wednesday | Sky Bet Championship |
| 11 | Tue 1 Oct 2019 | 91-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 12 | Fri 4 Oct 2019 | 91-2 v Birmingham CityBirmingham City 2-1 Middlesbrough | Sky Bet Championship |
| 13 | Sat 19 Oct 2019 | 90-1 v West Bromwich AlbionMiddlesbrough 0-1 West Bromwich Albion | Sky Bet Championship |
| 14 | Wed 23 Oct 2019 | 90-0 v Huddersfield TownHuddersfield Town 0-0 Middlesbrough | Sky Bet Championship |
| 15 | Sat 26 Oct 2019 | 90-0 v FulhamMiddlesbrough 0-0 Fulham | Sky Bet Championship |
| 16 | Sat 2 Nov 2019 | 90-2 v Derby CountyDerby County 2-0 Middlesbrough | Sky Bet Championship |
| 17 | Sat 9 Nov 2019 | 92-2 v Queens Park RangersQueens Park Rangers 2-2 Middlesbrough | Sky Bet Championship |
| 18 | Sun 24 Nov 2019 | 92-2 v Hull CityMiddlesbrough 2-2 Hull City | Sky Bet Championship |
| 19 | Wed 27 Nov 2019 | 91-0 v BarnsleyMiddlesbrough 1-0 Barnsley | Sky Bet Championship |
| 20 | Sat 30 Nov 2019 | 90-4 v Leeds UnitedLeeds United 4-0 Middlesbrough | Sky Bet Championship |
| 21 | Sat 7 Dec 2019 | 91-0 v Charlton AthleticMiddlesbrough 1-0 Charlton Athletic | Sky Bet Championship |
| 22 | Sat 1 Feb 2020 | 91-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 23 | Sat 8 Feb 2020 | 92-3 v BrentfordBrentford 3-2 Middlesbrough | Sky Bet Championship |
| 24 | Tue 11 Feb 2020 | 92-2 v Wigan AthleticWigan Athletic 2-2 Middlesbrough | Sky Bet Championship |
| 25 | Sat 15 Feb 2020 | 90-1 v Luton TownMiddlesbrough 0-1 Luton Town | Sky Bet Championship |
| 26 | Sat 22 Feb 2020 | 90-1 v BarnsleyBarnsley 1-0 Middlesbrough | Sky Bet Championship |
| 27 | Wed 26 Feb 2020 | 90-1 v Leeds UnitedMiddlesbrough 0-1 Leeds United | Sky Bet Championship |
| 28 | Sat 20 Jun 2020 | 90-3 v Swansea CityMiddlesbrough 0-3 Swansea City | Sky Bet Championship |
| 29 | Sat 27 Jun 2020 | 92-0 v Stoke CityStoke City 0-2 Middlesbrough | Sky Bet Championship |
| 30 | Thu 2 Jul 2020 | 91-2 v Hull CityHull City 2-1 Middlesbrough | Sky Bet Championship |
| 31 | Sun 5 Jul 2020 | 9 0-1 v Queens Park RangersMiddlesbrough 0-1 Queens Park Rangers | Sky Bet Championship |
| 32 | Wed 8 Jul 2020 | 9 2-0 v MillwallMillwall 0-2 Middlesbrough | Sky Bet Championship |
| 33 | Sat 11 Jul 2020 | 91-3 v Bristol CityMiddlesbrough 1-3 Bristol City | Sky Bet Championship |
| 34 | Tue 14 Jul 2020 | 92-1 v ReadingReading 1-2 Middlesbrough | Sky Bet Championship |
| 35 | Sat 18 Jul 2020 | 91-3 v Cardiff CityMiddlesbrough 1-3 Cardiff City | Sky Bet Championship |
| 36 | Wed 22 Jul 2020 | 92-1 v Sheffield WednesdaySheffield Wednesday 1-2 Middlesbrough | Sky Bet Championship |
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