| 1 | 11/9/2020 | 20-1 v WatfordWatford 1-0 Middlesbrough | Sky Bet Championship |
| 2 | 15/9/2020 | 20-2 v BarnsleyMiddlesbrough 0-2 Barnsley | Carabao Cup Second Round |
| 3 | 19/9/2020 | 21-1 v AFC BournemouthMiddlesbrough 1-1 AFC Bournemouth | Sky Bet Championship |
| 4 | 26/9/2020 | 2 1-1 v Queens Park RangersQueens Park Rangers 1-1 Middlesbrough | Sky Bet Championship |
| 5 | 3/10/2020 | 22-1 v BarnsleyMiddlesbrough 2-1 Barnsley | Sky Bet Championship |
| 6 | 17/10/2020 | 20-0 v ReadingMiddlesbrough 0-0 Reading | Sky Bet Championship |
| 7 | 20/10/2020 | 21-0 v Bristol CityBristol City 0-1 Middlesbrough | Sky Bet Championship |
| 8 | 24/10/2020 | 21-1 v Cardiff CityCardiff City 1-1 Middlesbrough | Sky Bet Championship |
| 9 | 27/10/2020 | 22-0 v Coventry CityMiddlesbrough 2-0 Coventry City | Sky Bet Championship |
| 10 | 31/10/2020 | 21-0 v Nottingham ForestMiddlesbrough 1-0 Nottingham Forest | Sky Bet Championship |
| 11 | 3/11/2020 | 20-0 v Blackburn RoversBlackburn Rovers 0-0 Middlesbrough | Sky Bet Championship |
| 12 | 7/11/2020 | 20-0 v BrentfordBrentford 0-0 Middlesbrough | Sky Bet Championship |
| 13 | 21/11/2020 | 20-1 v Norwich CityMiddlesbrough 0-1 Norwich City | Sky Bet Championship |
| 14 | 25/11/2020 | 23-0 v Derby CountyMiddlesbrough 3-0 Derby County | Sky Bet Championship |
| 15 | 28/11/2020 | 2 2-3 v Huddersfield TownHuddersfield Town 3-2 Middlesbrough | Sky Bet Championship |
| 16 | 12/12/2020 | 23-0 v MillwallMiddlesbrough 3-0 Millwall | Sky Bet Championship |
| 17 | 16/12/2020 | 21-0 v Luton TownMiddlesbrough 1-0 Luton Town | Sky Bet Championship |
| 18 | 19/12/2020 | 24-1 v Birmingham CityBirmingham City 1-4 Middlesbrough | Sky Bet Championship |
| 19 | 29/12/2020 | 21-2 v Sheffield WednesdaySheffield Wednesday 2-1 Middlesbrough | Sky Bet Championship |
| 20 | 2/1/2021 | 23-1 v Wycombe WanderersWycombe Wanderers 1-3 Middlesbrough | Sky Bet Championship |
| 21 | 16/1/2021 | 2 0-1 v Birmingham CityMiddlesbrough 0-1 Birmingham City | Sky Bet Championship |
| 22 | 20/1/2021 | 22-1 v Nottingham ForestNottingham Forest 1-2 Middlesbrough | Sky Bet Championship |
| 23 | 6/2/2021 | 21-4 v BrentfordMiddlesbrough 1-4 Brentford | Sky Bet Championship |
| 24 | 13/2/2021 | 2 1-2 v Derby CountyDerby County 2-1 Middlesbrough | Sky Bet Championship |
| 25 | 16/2/2021 | 22-1 v Huddersfield TownMiddlesbrough 2-1 Huddersfield Town | Sky Bet Championship |
| 26 | 20/2/2021 | 22-0 v ReadingReading 0-2 Middlesbrough | Sky Bet Championship |
| 27 | 23/2/2021 | 21-3 v Bristol CityMiddlesbrough 1-3 Bristol City | Sky Bet Championship |
| 28 | 27/2/2021 | 21-1 v Cardiff CityMiddlesbrough 1-1 Cardiff City | Sky Bet Championship |
| 29 | 2/3/2021 | 22-1 v Coventry CityCoventry City 1-2 Middlesbrough | Sky Bet Championship |
| 30 | 6/3/2021 | 21-2 v Swansea CitySwansea City 2-1 Middlesbrough | Sky Bet Championship |
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