| 1 | Fri 2 Aug 2019 | 53-3 v Luton TownLuton Town 3-3 Middlesbrough | Sky Bet Championship |
| 2 | Sat 10 Aug 2019 | 50-1 v BrentfordMiddlesbrough 0-1 Brentford | Sky Bet Championship |
| 3 | Sat 17 Aug 2019 | 50-1 v Blackburn RoversBlackburn Rovers 1-0 Middlesbrough | Sky Bet Championship |
| 4 | Tue 20 Aug 2019 | 51-0 v Wigan AthleticMiddlesbrough 1-0 Wigan Athletic | Sky Bet Championship |
| 5 | Sat 24 Aug 2019 | 51-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 6 | Sat 31 Aug 2019 | 52-2 v Bristol CityBristol City 2-2 Middlesbrough | Sky Bet Championship |
| 7 | Sat 14 Sep 2019 | 51-0 v ReadingMiddlesbrough 1-0 Reading | Sky Bet Championship |
| 8 | Sat 21 Sep 2019 | 50-1 v Cardiff CityCardiff City 1-0 Middlesbrough | Sky Bet Championship |
| 9 | Sat 28 Sep 2019 | 51-4 v Sheffield WednesdayMiddlesbrough 1-4 Sheffield Wednesday | Sky Bet Championship |
| 10 | Tue 1 Oct 2019 | 51-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 11 | Fri 4 Oct 2019 | 5 1-2 v Birmingham CityBirmingham City 2-1 Middlesbrough | Sky Bet Championship |
| 12 | Sat 19 Oct 2019 | 50-1 v West Bromwich AlbionMiddlesbrough 0-1 West Bromwich Albion | Sky Bet Championship |
| 13 | Wed 23 Oct 2019 | 50-0 v Huddersfield TownHuddersfield Town 0-0 Middlesbrough | Sky Bet Championship |
| 14 | Sat 22 Feb 2020 | 50-1 v BarnsleyBarnsley 1-0 Middlesbrough | Sky Bet Championship |
| 15 | Wed 26 Feb 2020 | 50-1 v Leeds UnitedMiddlesbrough 0-1 Leeds United | Sky Bet Championship |
| 16 | Mon 2 Mar 2020 | 5 2-2 v Nottingham ForestMiddlesbrough 2-2 Nottingham Forest | Sky Bet Championship |
| 17 | Sat 7 Mar 2020 | 5 1-0 v Charlton AthleticCharlton Athletic 0-1 Middlesbrough | Sky Bet Championship |
| 18 | Sat 20 Jun 2020 | 50-3 v Swansea CityMiddlesbrough 0-3 Swansea City | Sky Bet Championship |
| 19 | Sat 27 Jun 2020 | 52-0 v Stoke CityStoke City 0-2 Middlesbrough | Sky Bet Championship |
| 20 | Wed 8 Jul 2020 | 52-0 v MillwallMillwall 0-2 Middlesbrough | Sky Bet Championship |
| 21 | Sat 11 Jul 2020 | 51-3 v Bristol CityMiddlesbrough 1-3 Bristol City | Sky Bet Championship |
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