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