| 1 | Sat 30 Jul 2022 | 21-1 v West Bromwich AlbionMiddlesbrough 1-1 West Bromwich Albion | Sky Bet Championship |
| 2 | Sat 6 Aug 2022 | 22-3 v Queens Park RangersQueens Park Rangers 3-2 Middlesbrough | Sky Bet Championship |
| 3 | Sun 14 Aug 2022 | 22-2 v Sheffield UnitedMiddlesbrough 2-2 Sheffield United | Sky Bet Championship |
| 4 | Wed 17 Aug 2022 | 22-2 v Stoke CityStoke City 2-2 Middlesbrough | Sky Bet Championship |
| 5 | Sat 20 Aug 2022 | 2 0-1 v ReadingReading 1-0 Middlesbrough | Sky Bet Championship |
| 6 | Sat 27 Aug 2022 | 2 2-1 v Swansea CityMiddlesbrough 2-1 Swansea City | Sky Bet Championship |
| 7 | Tue 30 Aug 2022 | 2 1-2 v WatfordWatford 2-1 Middlesbrough | Sky Bet Championship |
| 8 | Mon 5 Sep 2022 | 2 1-0 v SunderlandMiddlesbrough 1-0 Sunderland | Sky Bet Championship |
| 9 | Tue 13 Sep 2022 | 22-3 v Cardiff CityMiddlesbrough 2-3 Cardiff City | Sky Bet Championship |
| 10 | Sat 17 Sep 2022 | 20-0 v Rotherham UnitedMiddlesbrough 0-0 Rotherham United | Sky Bet Championship |
| 11 | Sat 1 Oct 2022 | 2 0-1 v Coventry CityCoventry City 1-0 Middlesbrough | Sky Bet Championship |
| 12 | Sat 8 Oct 2022 | 2 0-2 v MillwallMillwall 2-0 Middlesbrough | Sky Bet Championship |
| 13 | Sat 15 Oct 2022 | 21-2 v Blackburn RoversMiddlesbrough 1-2 Blackburn Rovers | Sky Bet Championship |
| 14 | Wed 19 Oct 2022 | 24-1 v Wigan AthleticWigan Athletic 1-4 Middlesbrough | Sky Bet Championship |
| 15 | Sat 22 Oct 2022 | 20-0 v Huddersfield TownMiddlesbrough 0-0 Huddersfield Town | Sky Bet Championship |
| 16 | Sat 29 Oct 2022 | 21-2 v Preston North EndPreston North End 2-1 Middlesbrough | Sky Bet Championship |
| 17 | Tue 1 Nov 2022 | 2 3-1 v Hull CityHull City 1-3 Middlesbrough | Sky Bet Championship |
| 18 | Sat 5 Nov 2022 | 21-1 v Bristol CityMiddlesbrough 1-1 Bristol City | Sky Bet Championship |
| 19 | Tue 8 Nov 2022 | 23-0 v BlackpoolBlackpool 0-3 Middlesbrough | Sky Bet Championship |
| 20 | Sat 12 Nov 2022 | 22-1 v Norwich CityNorwich City 1-2 Middlesbrough | Sky Bet Championship |
| 21 | Sat 10 Dec 2022 | 22-1 v Luton TownMiddlesbrough 2-1 Luton Town | Sky Bet Championship |
| 22 | Sat 17 Dec 2022 | 21-3 v BurnleyBurnley 3-1 Middlesbrough | Sky Bet Championship |
| 23 | Mon 26 Dec 2022 | 24-1 v Wigan AthleticMiddlesbrough 4-1 Wigan Athletic | Sky Bet Championship |
| 24 | Thu 29 Dec 2022 | 22-1 v Blackburn RoversBlackburn Rovers 1-2 Middlesbrough | Sky Bet Championship |
| 25 | Mon 2 Jan 2023 | 23-1 v Birmingham CityBirmingham City 1-3 Middlesbrough | Sky Bet Championship |
| 26 | Sat 7 Jan 2023 | 21-5 v Brighton & Hove AlbionMiddlesbrough 1-5 Brighton & Hove Albion | Emirates FA Cup Third Round |
| 27 | Sat 4 Feb 2023 | 23-0 v BlackpoolMiddlesbrough 3-0 Blackpool | Sky Bet Championship |
| 28 | Sat 11 Feb 2023 | 23-1 v Cardiff CityCardiff City 1-3 Middlesbrough | Sky Bet Championship |
| 29 | Sat 25 Feb 2023 | 20-2 v West Bromwich AlbionWest Bromwich Albion 2-0 Middlesbrough | Sky Bet Championship |
| 30 | Sat 4 Mar 2023 | 25-0 v ReadingMiddlesbrough 5-0 Reading | Sky Bet Championship |
| 31 | Fri 14 Apr 2023 | 25-1 v Norwich CityMiddlesbrough 5-1 Norwich City | Sky Bet Championship |
| 32 | Wed 19 Apr 2023 | 23-1 v Hull CityMiddlesbrough 3-1 Hull City | Sky Bet Championship |
| 33 | Mon 24 Apr 2023 | 21-2 v Luton TownLuton Town 2-1 Middlesbrough | Sky Bet Championship |
| 34 | Mon 1 May 2023 | 20-1 v Rotherham UnitedRotherham United 1-0 Middlesbrough | Sky Bet Championship |
| 35 | Mon 8 May 2023 | 2 1-1 v Coventry CityMiddlesbrough 1-1 Coventry City | Sky Bet Championship |
| 36 | Sun 14 May 2023 | 20-0 v Coventry CityCoventry City 0-0 Middlesbrough | Sky Bet Championship Play-off Semi Final |
| 37 | Wed 17 May 2023 | 2 0-1 v Coventry CityMiddlesbrough 0-1 Coventry City | Sky Bet Championship Play-off Semi Final |
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