| 1 | Sun 8 Aug 2021 | 161-1 v FulhamFulham 1-1 Middlesbrough | Sky Bet Championship |
| 2 | Sat 14 Aug 2021 | 162-1 v Bristol CityMiddlesbrough 2-1 Bristol City | Sky Bet Championship |
| 3 | Wed 18 Aug 2021 | 162-3 v Queens Park RangersMiddlesbrough 2-3 Queens Park Rangers | Sky Bet Championship |
| 4 | Sat 21 Aug 2021 | 160-0 v Derby CountyDerby County 0-0 Middlesbrough | Sky Bet Championship |
| 5 | Sat 28 Aug 2021 | 161-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 6 | Sat 11 Sep 2021 | 16 0-2 v Coventry CityCoventry City 2-0 Middlesbrough | Sky Bet Championship |
| 7 | Wed 15 Sep 2021 | 16 2-0 v Nottingham ForestNottingham Forest 0-2 Middlesbrough | Sky Bet Championship |
| 8 | Sat 18 Sep 2021 | 161-2 v BlackpoolMiddlesbrough 1-2 Blackpool | Sky Bet Championship |
| 9 | Sat 25 Sep 2021 | 160-1 v ReadingReading 1-0 Middlesbrough | Sky Bet Championship |
| 10 | Tue 28 Sep 2021 | 162-0 v Sheffield UnitedMiddlesbrough 2-0 Sheffield United | Sky Bet Championship |
| 11 | Sat 2 Oct 2021 | 160-2 v Hull CityHull City 2-0 Middlesbrough | Sky Bet Championship |
| 12 | Sat 16 Oct 2021 | 162-0 v Peterborough UnitedMiddlesbrough 2-0 Peterborough United | Sky Bet Championship |
| 13 | Wed 20 Oct 2021 | 162-0 v BarnsleyMiddlesbrough 2-0 Barnsley | Sky Bet Championship |
| 14 | Sat 23 Oct 2021 | 162-0 v Cardiff CityCardiff City 0-2 Middlesbrough | Sky Bet Championship |
| 15 | Sat 30 Oct 2021 | 160-2 v Birmingham CityMiddlesbrough 0-2 Birmingham City | Sky Bet Championship |
| 16 | Tue 2 Nov 2021 | 161-3 v Luton TownLuton Town 3-1 Middlesbrough | Sky Bet Championship |
| 17 | Sat 6 Nov 2021 | 16 1-1 v West Bromwich AlbionWest Bromwich Albion 1-1 Middlesbrough | Sky Bet Championship |
| 18 | Sat 20 Nov 2021 | 16 1-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 19 | Tue 23 Nov 2021 | 161-2 v Preston North EndMiddlesbrough 1-2 Preston North End | Sky Bet Championship |
| 20 | Sat 27 Nov 2021 | 162-1 v Huddersfield TownHuddersfield Town 1-2 Middlesbrough | Sky Bet Championship |
| 21 | Sat 4 Dec 2021 | 161-0 v Swansea CityMiddlesbrough 1-0 Swansea City | Sky Bet Championship |
| 22 | Sat 11 Dec 2021 | 160-0 v Stoke CityStoke City 0-0 Middlesbrough | Sky Bet Championship |
| 23 | Sat 18 Dec 2021 | 161-0 v AFC BournemouthMiddlesbrough 1-0 AFC Bournemouth | Sky Bet Championship |
| 24 | Sun 26 Dec 2021 | 16 2-0 v Nottingham ForestMiddlesbrough 2-0 Nottingham Forest | Sky Bet Championship |
| 25 | Sat 8 Jan 2022 | 163-2 v Mansfield TownMansfield Town 2-3 Middlesbrough | Emirates FA Cup Third Round |
| 26 | Sat 15 Jan 2022 | 162-1 v ReadingMiddlesbrough 2-1 Reading | Sky Bet Championship |
| 27 | Mon 24 Jan 2022 | 160-1 v Blackburn RoversBlackburn Rovers 1-0 Middlesbrough | Sky Bet Championship |
| 28 | Sat 29 Jan 2022 | 161-0 v Coventry CityMiddlesbrough 1-0 Coventry City | Sky Bet Championship |
| 29 | Fri 4 Feb 2022 | 161-1 v Manchester UnitedManchester United 1-1 Middlesbrough | Emirates FA Cup Fourth Round |
| 30 | Wed 9 Feb 2022 | 16 2-2 v Queens Park RangersQueens Park Rangers 2-2 Middlesbrough | Sky Bet Championship |
| 31 | Sat 12 Feb 2022 | 16 4-1 v Derby CountyMiddlesbrough 4-1 Derby County | Sky Bet Championship |
| 32 | Sat 19 Feb 2022 | 161-2 v Bristol CityBristol City 2-1 Middlesbrough | Sky Bet Championship |
| 33 | Tue 22 Feb 2022 | 16 2-1 v West Bromwich AlbionMiddlesbrough 2-1 West Bromwich Albion | Sky Bet Championship |
| 34 | Sat 26 Feb 2022 | 162-3 v BarnsleyBarnsley 3-2 Middlesbrough | Sky Bet Championship |
| 35 | Tue 1 Mar 2022 | 161-0 v Tottenham HotspurMiddlesbrough 1-0 Tottenham Hotspur | Emirates FA Cup Fifth Round |
| 36 | Sat 5 Mar 2022 | 162-1 v Luton TownMiddlesbrough 2-1 Luton Town | Sky Bet Championship |
| 37 | Tue 8 Mar 2022 | 16 1-4 v Sheffield UnitedSheffield United 4-1 Middlesbrough | Sky Bet Championship |
| 38 | Sat 12 Mar 2022 | 160-0 v MillwallMillwall 0-0 Middlesbrough | Sky Bet Championship |
| 39 | Tue 15 Mar 2022 | 162-0 v Birmingham CityBirmingham City 0-2 Middlesbrough | Sky Bet Championship |
| 40 | Sat 19 Mar 2022 | 16 0-2 v ChelseaMiddlesbrough 0-2 Chelsea | Emirates FA Cup Sixth Round |
| 41 | Sat 2 Apr 2022 | 164-0 v Peterborough UnitedPeterborough United 0-4 Middlesbrough | Sky Bet Championship |
| 42 | Wed 6 Apr 2022 | 160-1 v FulhamMiddlesbrough 0-1 Fulham | Sky Bet Championship |
| 43 | Sat 9 Apr 2022 | 160-1 v Hull CityMiddlesbrough 0-1 Hull City | Sky Bet Championship |
| 44 | Fri 15 Apr 2022 | 160-0 v AFC BournemouthAFC Bournemouth 0-0 Middlesbrough | Sky Bet Championship |
| 45 | Mon 18 Apr 2022 | 160-2 v Huddersfield TownMiddlesbrough 0-2 Huddersfield Town | Sky Bet Championship |
| 46 | Sat 23 Apr 2022 | 161-1 v Swansea CitySwansea City 1-1 Middlesbrough | Sky Bet Championship |
| 47 | Wed 27 Apr 2022 | 16 2-0 v Cardiff CityMiddlesbrough 2-0 Cardiff City | Sky Bet Championship |
| 48 | Sat 30 Apr 2022 | 163-1 v Stoke CityMiddlesbrough 3-1 Stoke City | Sky Bet Championship |
| 49 | Sat 7 May 2022 | 161-4 v Preston North EndPreston North End 4-1 Middlesbrough | Sky Bet Championship |
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