| 1 | Wed 11 Aug 2021 | 140-3 v BlackpoolBlackpool 3-0 Middlesbrough | Carabao Cup First Round |
| 2 | Sat 21 Aug 2021 | 14 0-0 v Derby CountyDerby County 0-0 Middlesbrough | Sky Bet Championship |
| 3 | Wed 15 Sep 2021 | 14 2-0 v Nottingham ForestNottingham Forest 0-2 Middlesbrough | Sky Bet Championship |
| 4 | Sat 18 Sep 2021 | 141-2 v BlackpoolMiddlesbrough 1-2 Blackpool | Sky Bet Championship |
| 5 | Sat 25 Sep 2021 | 14 0-1 v ReadingReading 1-0 Middlesbrough | Sky Bet Championship |
| 6 | Tue 28 Sep 2021 | 14 2-0 v Sheffield UnitedMiddlesbrough 2-0 Sheffield United | Sky Bet Championship |
| 7 | Sat 2 Oct 2021 | 14 0-2 v Hull CityHull City 2-0 Middlesbrough | Sky Bet Championship |
| 8 | Wed 20 Oct 2021 | 14 2-0 v BarnsleyMiddlesbrough 2-0 Barnsley | Sky Bet Championship |
| 9 | Sat 23 Oct 2021 | 142-0 v Cardiff CityCardiff City 0-2 Middlesbrough | Sky Bet Championship |
| 10 | Sat 30 Oct 2021 | 140-2 v Birmingham CityMiddlesbrough 0-2 Birmingham City | Sky Bet Championship |
| 11 | Sat 6 Nov 2021 | 14 1-1 v West Bromwich AlbionWest Bromwich Albion 1-1 Middlesbrough | Sky Bet Championship |
| 12 | Sat 20 Nov 2021 | 141-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 13 | Tue 23 Nov 2021 | 141-2 v Preston North EndMiddlesbrough 1-2 Preston North End | Sky Bet Championship |
| 14 | Sun 26 Dec 2021 | 142-0 v Nottingham ForestMiddlesbrough 2-0 Nottingham Forest | Sky Bet Championship |
| 15 | Wed 29 Dec 2021 | 14 2-1 v BlackpoolBlackpool 1-2 Middlesbrough | Sky Bet Championship |
| 16 | Sat 8 Jan 2022 | 143-2 v Mansfield TownMansfield Town 2-3 Middlesbrough | Emirates FA Cup Third Round |
| 17 | Fri 4 Feb 2022 | 141-1 v Manchester UnitedManchester United 1-1 Middlesbrough | Emirates FA Cup Fourth Round |
| 18 | Tue 22 Feb 2022 | 142-1 v West Bromwich AlbionMiddlesbrough 2-1 West Bromwich Albion | Sky Bet Championship |
| 19 | Tue 1 Mar 2022 | 141-0 v Tottenham HotspurMiddlesbrough 1-0 Tottenham Hotspur | Emirates FA Cup Fifth Round |
| 20 | Tue 8 Mar 2022 | 14 1-4 v Sheffield UnitedSheffield United 4-1 Middlesbrough | Sky Bet Championship |
| 21 | Sat 12 Mar 2022 | 140-0 v MillwallMillwall 0-0 Middlesbrough | Sky Bet Championship |
| 22 | Tue 15 Mar 2022 | 142-0 v Birmingham CityBirmingham City 0-2 Middlesbrough | Sky Bet Championship |
| 23 | Sat 19 Mar 2022 | 14 0-2 v ChelseaMiddlesbrough 0-2 Chelsea | Emirates FA Cup Sixth Round |
| 24 | Wed 6 Apr 2022 | 140-1 v FulhamMiddlesbrough 0-1 Fulham | Sky Bet Championship |
| 25 | Sat 30 Apr 2022 | 143-1 v Stoke CityMiddlesbrough 3-1 Stoke City | Sky Bet Championship |
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