| 1 | Sat 13 Jan 2024 | 123-1 v MillwallMillwall 1-3 Middlesbrough | Sky Bet Championship |
| 2 | Sat 20 Jan 2024 | 121-1 v Rotherham UnitedMiddlesbrough 1-1 Rotherham United | Sky Bet Championship |
| 3 | Sun 4 Feb 2024 | 12 1-1 v SunderlandMiddlesbrough 1-1 Sunderland | Sky Bet Championship |
| 4 | Sat 10 Feb 2024 | 121-2 v Bristol CityMiddlesbrough 1-2 Bristol City | Sky Bet Championship |
| 5 | Wed 14 Feb 2024 | 121-2 v Preston North EndPreston North End 2-1 Middlesbrough | Sky Bet Championship |
| 6 | Sat 17 Feb 2024 | 12 2-1 v Leicester CityLeicester City 1-2 Middlesbrough | Sky Bet Championship |
| 7 | Sat 24 Feb 2024 | 12 0-2 v Plymouth ArgyleMiddlesbrough 0-2 Plymouth Argyle | Sky Bet Championship |
| 8 | Sat 2 Mar 2024 | 120-2 v Stoke CityStoke City 2-0 Middlesbrough | Sky Bet Championship |
| 9 | Wed 6 Mar 2024 | 123-1 v Norwich CityMiddlesbrough 3-1 Norwich City | Sky Bet Championship |
| 10 | Sat 9 Mar 2024 | 12 2-0 v Queens Park RangersQueens Park Rangers 0-2 Middlesbrough | Sky Bet Championship |
| 11 | Tue 12 Mar 2024 | 121-0 v Birmingham CityBirmingham City 0-1 Middlesbrough | Sky Bet Championship |
| 12 | Sat 16 Mar 2024 | 12 0-0 v Blackburn RoversMiddlesbrough 0-0 Blackburn Rovers | Sky Bet Championship |
| 13 | Fri 29 Mar 2024 | 121-1 v SouthamptonSouthampton 1-1 Middlesbrough | Sky Bet Championship |
| 14 | Mon 1 Apr 2024 | 122-0 v Sheffield WednesdayMiddlesbrough 2-0 Sheffield Wednesday | Sky Bet Championship |
| 15 | Sat 6 Apr 2024 | 12 2-0 v Swansea CityMiddlesbrough 2-0 Swansea City | Sky Bet Championship |
| 16 | Wed 10 Apr 2024 | 122-2 v Hull CityHull City 2-2 Middlesbrough | Sky Bet Championship |
| 17 | Sat 13 Apr 2024 | 12 1-1 v Ipswich TownIpswich Town 1-1 Middlesbrough | Sky Bet Championship |
| 18 | Sat 27 Apr 2024 | 124-1 v Cardiff CityCardiff City 1-4 Middlesbrough | Sky Bet Championship |
| 19 | Sat 4 May 2024 | 123-1 v WatfordMiddlesbrough 3-1 Watford | Sky Bet Championship |
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