| 1 | Sat 5 Aug 2023 | 100-1 v MillwallMiddlesbrough 0-1 Millwall | Sky Bet Championship |
| 2 | Sat 12 Aug 2023 | 100-3 v Coventry CityCoventry City 3-0 Middlesbrough | Sky Bet Championship |
| 3 | Sat 19 Aug 2023 | 101-1 v Huddersfield TownMiddlesbrough 1-1 Huddersfield Town | Sky Bet Championship |
| 4 | Sat 26 Aug 2023 | 10 2-4 v West Bromwich AlbionWest Bromwich Albion 4-2 Middlesbrough | Sky Bet Championship |
| 5 | Tue 29 Aug 2023 | 103-1 v Bolton WanderersBolton Wanderers 1-3 Middlesbrough | Carabao Cup Second Round |
| 6 | Sat 2 Sep 2023 | 100-2 v Queens Park RangersMiddlesbrough 0-2 Queens Park Rangers | Sky Bet Championship |
| 7 | Sat 16 Sep 2023 | 101-2 v Blackburn RoversBlackburn Rovers 2-1 Middlesbrough | Sky Bet Championship |
| 8 | Tue 19 Sep 2023 | 101-1 v Sheffield WednesdaySheffield Wednesday 1-1 Middlesbrough | Sky Bet Championship |
| 9 | Tue 26 Sep 2023 | 102-0 v Bradford CityBradford City 0-2 Middlesbrough | Carabao Cup Third Round |
| 10 | Tue 3 Oct 2023 | 102-0 v Cardiff CityMiddlesbrough 2-0 Cardiff City | Sky Bet Championship |
| 11 | Sat 7 Oct 2023 | 104-0 v SunderlandSunderland 0-4 Middlesbrough | Sky Bet Championship |
| 12 | Sat 21 Oct 2023 | 101-0 v Birmingham CityMiddlesbrough 1-0 Birmingham City | Sky Bet Championship |
| 13 | Tue 24 Oct 2023 | 102-1 v Norwich CityNorwich City 1-2 Middlesbrough | Sky Bet Championship |
| 14 | Sat 28 Oct 2023 | 100-2 v Stoke CityMiddlesbrough 0-2 Stoke City | Sky Bet Championship |
| 15 | Tue 31 Oct 2023 | 10 3-2 v Exeter CityExeter City 2-3 Middlesbrough | Carabao Cup Fourth Round |
| 16 | Sat 4 Nov 2023 | 103-3 v Plymouth ArgylePlymouth Argyle 3-3 Middlesbrough | Sky Bet Championship |
| 17 | Sat 11 Nov 2023 | 10 1-0 v Leicester CityMiddlesbrough 1-0 Leicester City | Sky Bet Championship |
| 18 | Sat 25 Nov 2023 | 102-3 v Bristol CityBristol City 3-2 Middlesbrough | Sky Bet Championship |
| 19 | Tue 28 Nov 2023 | 104-0 v Preston North EndMiddlesbrough 4-0 Preston North End | Sky Bet Championship |
| 20 | Sat 2 Dec 2023 | 10 2-3 v Leeds UnitedLeeds United 3-2 Middlesbrough | Sky Bet Championship |
| 21 | Sat 9 Dec 2023 | 100-2 v Ipswich TownMiddlesbrough 0-2 Ipswich Town | Sky Bet Championship |
| 22 | Wed 13 Dec 2023 | 101-2 v Hull CityMiddlesbrough 1-2 Hull City | Sky Bet Championship |
| 23 | Sat 16 Dec 2023 | 102-1 v Swansea CitySwansea City 1-2 Middlesbrough | Sky Bet Championship |
| 24 | Tue 19 Dec 2023 | 10 3-0 v Port ValePort Vale 0-3 Middlesbrough | Carabao Cup Quarter Final |
| 25 | Sat 23 Dec 2023 | 101-0 v West Bromwich AlbionMiddlesbrough 1-0 West Bromwich Albion | Sky Bet Championship |
| 26 | Tue 26 Dec 2023 | 100-1 v Rotherham UnitedRotherham United 1-0 Middlesbrough | Sky Bet Championship |
| 27 | Fri 29 Dec 2023 | 10 2-1 v Huddersfield TownHuddersfield Town 1-2 Middlesbrough | Sky Bet Championship |
| 28 | Mon 1 Jan 2024 | 10 1-3 v Coventry CityMiddlesbrough 1-3 Coventry City | Sky Bet Championship |
| 29 | Sat 6 Jan 2024 | 100-1 v Aston VillaMiddlesbrough 0-1 Aston Villa | Emirates FA Cup Third Round |
| 30 | Sat 13 Jan 2024 | 103-1 v MillwallMillwall 1-3 Middlesbrough | Sky Bet Championship |
| 31 | Sat 20 Jan 2024 | 101-1 v Rotherham UnitedMiddlesbrough 1-1 Rotherham United | Sky Bet Championship |
| 32 | Tue 23 Jan 2024 | 101-6 v ChelseaChelsea 6-1 Middlesbrough | Carabao Cup Semi Final |
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