| August 2023Aug 05 |  Championship | Middlesbrough 0–1 MillwallRegular Season - 1 | L |
| Aug 08 |  EFL Cup | Huddersfield 2–3Middlesbrough1st Round | W |
| Aug 12 | Championship | Coventry 3–0MiddlesbroughRegular Season - 2 | L |
| Aug 19 | Championship | Middlesbrough1–1HuddersfieldRegular Season - 3 | D |
| Aug 26 | Championship | West Brom 4–2MiddlesbroughRegular Season - 4 | L |
| Aug 29 | EFL Cup | Bolton 1–3Middlesbrough2nd Round | W |
| September 2023Sep 02 | Championship | Middlesbrough0–2 QPRRegular Season - 5 | L |
| Sep 16 | Championship | Blackburn 2–1MiddlesbroughRegular Season - 6 | L |
| Sep 19 | Championship | Sheffield Wednesday 1–1MiddlesbroughRegular Season - 7 | D |
| Sep 23 | Championship | Middlesbrough2–1 SouthamptonRegular Season - 8 | W |
| Sep 26 | EFL Cup | Bradford 0–2Middlesbrough3rd Round | W |
| Sep 30 | Championship | Watford 2–3MiddlesbroughRegular Season - 9 | W |
| October 2023Oct 03 | Championship | Middlesbrough2–0 CardiffRegular Season - 10 | W |
| Oct 07 | Championship | Sunderland 0–4MiddlesbroughRegular Season - 11 | W |
| Oct 21 | Championship | Middlesbrough1–0 BirminghamRegular Season - 12 | W |
| Oct 24 | Championship | Norwich 1–2MiddlesbroughRegular Season - 13 | W |
| Oct 28 | Championship | Middlesbrough0–2 Stoke CityRegular Season - 14 | L |
| Oct 31 | EFL Cup | Exeter City 2–3MiddlesbroughRound of 16 | W |
| November 2023Nov 04 | Championship | Plymouth 3–3MiddlesbroughRegular Season - 15 | D |
| Nov 11 | Championship | Middlesbrough1–0 LeicesterRegular Season - 16 | W |
| Nov 25 | Championship | Bristol City 3–2MiddlesbroughRegular Season - 17 | L |
| Nov 28 | Championship | Middlesbrough4–0 PrestonRegular Season - 18 | W |
| December 2023Dec 02 | Championship | Leeds 3–2MiddlesbroughRegular Season - 19 | L |
| Dec 09 | Championship | Middlesbrough0–2 IpswichRegular Season - 20 | L |
| Dec 13 | Championship | Middlesbrough1–2 Hull CityRegular Season - 21 | L |
| Dec 16 | Championship | Swansea 1–2MiddlesbroughRegular Season - 22 | W |
| Dec 19 | EFL Cup | Port Vale 0–3MiddlesbroughQuarter-finals | W |
| Dec 23 | Championship | Middlesbrough1–0West BromRegular Season - 23 | W |
| Dec 26 | Championship | Rotherham 1–0MiddlesbroughRegular Season - 24 | L |
| Dec 29 | Championship | Huddersfield1–2MiddlesbroughRegular Season - 25 | W |
| January 2024Jan 01 | Championship | Middlesbrough1–3CoventryRegular Season - 26 | L |
| Jan 06 |  FA Cup | Middlesbrough0–1 Aston Villa3rd Round | L |
| Jan 09 | EFL Cup | Middlesbrough1–0 ChelseaSemi-finals | W |
| Jan 13 | Championship | Millwall1–3MiddlesbroughRegular Season - 27 | W |
| Jan 20 | Championship | Middlesbrough1–1RotherhamRegular Season - 28 | D |
| Jan 23 | EFL Cup | Chelsea6–1MiddlesbroughSemi-finals | L |
| February 2024Feb 04 | Championship | Middlesbrough1–1SunderlandRegular Season - 30 | D |
| Feb 10 | Championship | Middlesbrough1–2Bristol CityRegular Season - 31 | L |
| Feb 14 | Championship | Preston2–1MiddlesbroughRegular Season - 32 | L |
| Feb 17 | Championship | Leicester1–2MiddlesbroughRegular Season - 33 | W |
| Feb 24 | Championship | Middlesbrough0–2PlymouthRegular Season - 34 | L |
| March 2024Mar 02 | Championship | Stoke City2–0MiddlesbroughRegular Season - 35 | L |
| Mar 06 | Championship | Middlesbrough3–1NorwichRegular Season - 36 | W |
| Mar 09 | Championship | QPR0–2MiddlesbroughRegular Season - 37 | W |
| Mar 12 | Championship | Birmingham0–1MiddlesbroughRegular Season - 29 | W |
| Mar 16 | Championship | Middlesbrough0–0BlackburnRegular Season - 38 | D |
| Mar 29 | Championship | Southampton1–1MiddlesbroughRegular Season - 39 | D |
| April 2024Apr 01 | Championship | Middlesbrough2–0Sheffield WednesdayRegular Season - 40 | W |
| Apr 06 | Championship | Middlesbrough2–0SwanseaRegular Season - 41 | W |
| Apr 10 | Championship | Hull City2–2MiddlesbroughRegular Season - 42 | D |
| Apr 13 | Championship | Ipswich1–1MiddlesbroughRegular Season - 43 | D |
| Apr 22 | Championship | Middlesbrough3–4LeedsRegular Season - 44 | L |
| Apr 27 | Championship | Cardiff1–4MiddlesbroughRegular Season - 45 | W |
| May 2024May 04 | Championship | Middlesbrough3–1WatfordRegular Season - 46 | W |
