| julio de 202230 jul |  Championship | Middlesbrough 1–1 West BromRegular Season - 1 | E |
| agosto de 202206 ago | Championship | QPR 3–2MiddlesbroughRegular Season - 2 | D |
| 10 ago |  EFL Cup | Middlesbrough0–1 Barnsley1st Round | D |
| 14 ago | Championship | Middlesbrough2–2 Sheffield UtdRegular Season - 3 | E |
| 17 ago | Championship | Stoke City 2–2MiddlesbroughRegular Season - 4 | E |
| 20 ago | Championship | Reading 1–0MiddlesbroughRegular Season - 5 | D |
| 27 ago | Championship | Middlesbrough2–1 SwanseaRegular Season - 6 | V |
| 30 ago | Championship | Watford 2–1MiddlesbroughRegular Season - 7 | D |
| septiembre de 202205 sept | Championship | Middlesbrough1–0 SunderlandRegular Season - 8 | V |
| 13 sept | Championship | Middlesbrough2–3 CardiffRegular Season - 10 | D |
| 17 sept | Championship | Middlesbrough0–0 RotherhamRegular Season - 11 | E |
| octubre de 202201 oct | Championship | Coventry 1–0MiddlesbroughRegular Season - 12 | D |
| 05 oct | Championship | Middlesbrough1–0 BirminghamRegular Season - 13 | V |
| 08 oct | Championship | Millwall 2–0MiddlesbroughRegular Season - 14 | D |
| 15 oct | Championship | Middlesbrough1–2 BlackburnRegular Season - 15 | D |
| 19 oct | Championship | Wigan 1–4MiddlesbroughRegular Season - 16 | V |
| 22 oct | Championship | Middlesbrough0–0 HuddersfieldRegular Season - 17 | E |
| 29 oct | Championship | Preston 2–1MiddlesbroughRegular Season - 18 | D |
| noviembre de 202201 nov | Championship | Hull City 1–3MiddlesbroughRegular Season - 19 | V |
| 05 nov | Championship | Middlesbrough1–1 Bristol CityRegular Season - 20 | E |
| 08 nov | Championship | Blackpool 0–3MiddlesbroughRegular Season - 9 | V |
| 12 nov | Championship | Norwich 1–2MiddlesbroughRegular Season - 21 | V |
| diciembre de 202210 dic | Championship | Middlesbrough2–1 LutonRegular Season - 22 | V |
| 17 dic | Championship | Burnley 3–1MiddlesbroughRegular Season - 23 | D |
| 26 dic | Championship | Middlesbrough4–1WiganRegular Season - 24 | V |
| 29 dic | Championship | Blackburn1–2MiddlesbroughRegular Season - 25 | V |
| enero de 202302 ene | Championship | Birmingham1–3MiddlesbroughRegular Season - 26 | V |
| 07 ene |  FA Cup | Middlesbrough1–5 Brighton3rd Round | D |
| 14 ene | Championship | Middlesbrough1–0MillwallRegular Season - 27 | V |
| 22 ene | Championship | Sunderland2–0MiddlesbroughRegular Season - 28 | D |
| 28 ene | Championship | Middlesbrough2–0WatfordRegular Season - 29 | V |
| febrero de 202304 feb | Championship | Middlesbrough3–0BlackpoolRegular Season - 30 | V |
| 11 feb | Championship | Cardiff1–3MiddlesbroughRegular Season - 31 | V |
| 15 feb | Championship | Sheffield Utd1–3MiddlesbroughRegular Season - 32 | V |
| 18 feb | Championship | Middlesbrough3–1QPRRegular Season - 33 | V |
| 25 feb | Championship | West Brom2–0MiddlesbroughRegular Season - 34 | D |
| marzo de 202304 mar | Championship | Middlesbrough5–0ReadingRegular Season - 35 | V |
| 11 mar | Championship | Swansea1–3MiddlesbroughRegular Season - 36 | V |
| 14 mar | Championship | Middlesbrough1–1Stoke CityRegular Season - 37 | E |
| 18 mar | Championship | Middlesbrough4–0PrestonRegular Season - 38 | V |
| abril de 202301 abr | Championship | Huddersfield4–2MiddlesbroughRegular Season - 39 | D |
| 07 abr | Championship | Middlesbrough1–2BurnleyRegular Season - 40 | D |
| 10 abr | Championship | Bristol City2–2MiddlesbroughRegular Season - 41 | E |
| 14 abr | Championship | Middlesbrough5–1NorwichRegular Season - 42 | V |
| 19 abr | Championship | Middlesbrough3–1Hull CityRegular Season - 43 | V |
| 24 abr | Championship | Luton2–1MiddlesbroughRegular Season - 44 | D |
| mayo de 202301 may | Championship | Rotherham1–0MiddlesbroughRegular Season - 45 | D |
| 08 may | Championship | Middlesbrough1–1CoventryRegular Season - 46 | E |
| 14 may | Championship | Coventry0–0MiddlesbroughPromotion Play-offs - Semi-finals | E |
| 17 may | Championship | Middlesbrough0–1CoventryPromotion Play-offs - Semi-finals | D |
