| 1 | Wed 11 Aug 2021 | 10 0-3 v BlackpoolBlackpool 3-0 Middlesbrough | Carabao Cup First Round |
| 2 | Sat 14 Aug 2021 | 102-1 v Bristol CityMiddlesbrough 2-1 Bristol City | Sky Bet Championship |
| 3 | Sat 18 Sep 2021 | 101-2 v BlackpoolMiddlesbrough 1-2 Blackpool | Sky Bet Championship |
| 4 | Sat 25 Sep 2021 | 100-1 v ReadingReading 1-0 Middlesbrough | Sky Bet Championship |
| 5 | Sat 16 Oct 2021 | 10 2-0 v Peterborough UnitedMiddlesbrough 2-0 Peterborough United | Sky Bet Championship |
| 6 | Wed 20 Oct 2021 | 102-0 v BarnsleyMiddlesbrough 2-0 Barnsley | Sky Bet Championship |
| 7 | Sat 23 Oct 2021 | 102-0 v Cardiff CityCardiff City 0-2 Middlesbrough | Sky Bet Championship |
| 8 | Sat 30 Oct 2021 | 100-2 v Birmingham CityMiddlesbrough 0-2 Birmingham City | Sky Bet Championship |
| 9 | Sat 6 Nov 2021 | 101-1 v West Bromwich AlbionWest Bromwich Albion 1-1 Middlesbrough | Sky Bet Championship |
| 10 | Sun 26 Dec 2021 | 102-0 v Nottingham ForestMiddlesbrough 2-0 Nottingham Forest | Sky Bet Championship |
| 11 | Sat 29 Jan 2022 | 101-0 v Coventry CityMiddlesbrough 1-0 Coventry City | Sky Bet Championship |
| 12 | Fri 4 Feb 2022 | 101-1 v Manchester UnitedManchester United 1-1 Middlesbrough | Emirates FA Cup Fourth Round |
| 13 | Wed 9 Feb 2022 | 102-2 v Queens Park RangersQueens Park Rangers 2-2 Middlesbrough | Sky Bet Championship |
| 14 | Sat 23 Apr 2022 | 101-1 v Swansea CitySwansea City 1-1 Middlesbrough | Sky Bet Championship |
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