| 1 | Tue 29 Aug | 233-1 v Bolton WanderersBolton Wanderers 1-3 Middlesbrough | Carabao Cup Second Round |
| 2 | Tue 26 Sep | 232-0 v Bradford CityBradford City 0-2 Middlesbrough | Carabao Cup Third Round |
| 3 | Tue 31 Oct | 233-2 v Exeter CityExeter City 2-3 Middlesbrough | Carabao Cup Fourth Round |
| 4 | Sat 16 Dec | 232-1 v Swansea CitySwansea City 1-2 Middlesbrough | Sky Bet Championship |
| 5 | Tue 19 Dec | 233-0 v Port ValePort Vale 0-3 Middlesbrough | Carabao Cup Quarter Final |
| 6 | Sat 23 Dec | 231-0 v West Bromwich AlbionMiddlesbrough 1-0 West Bromwich Albion | Sky Bet Championship |
| 7 | Tue 26 Dec | 230-1 v Rotherham UnitedRotherham United 1-0 Middlesbrough | Sky Bet Championship |
| 8 | Fri 29 Dec | 232-1 v Huddersfield TownHuddersfield Town 1-2 Middlesbrough | Sky Bet Championship |
| 9 | Mon 1 Jan | 231-3 v Coventry CityMiddlesbrough 1-3 Coventry City | Sky Bet Championship |
| 10 | Sat 6 Jan | 230-1 v Aston VillaMiddlesbrough 0-1 Aston Villa | Emirates FA Cup Third Round |
| 11 | Tue 9 Jan | 231-0 v ChelseaMiddlesbrough 1-0 Chelsea | Carabao Cup Semi Final |
| 12 | Sat 13 Jan | 233-1 v MillwallMillwall 1-3 Middlesbrough | Sky Bet Championship |
| 13 | Sat 20 Jan | 231-1 v Rotherham UnitedMiddlesbrough 1-1 Rotherham United | Sky Bet Championship |
| 14 | Tue 23 Jan | 231-6 v ChelseaChelsea 6-1 Middlesbrough | Carabao Cup Semi Final |
| 15 | Sun 4 Feb | 231-1 v SunderlandMiddlesbrough 1-1 Sunderland | Sky Bet Championship |
| 16 | Sat 10 Feb | 231-2 v Bristol CityMiddlesbrough 1-2 Bristol City | Sky Bet Championship |
| 17 | Wed 14 Feb | 231-2 v Preston North EndPreston North End 2-1 Middlesbrough | Sky Bet Championship |
| 18 | Sat 17 Feb | 23 2-1 v Leicester CityLeicester City 1-2 Middlesbrough | Sky Bet Championship |
| 19 | Sat 24 Feb | 230-2 v Plymouth ArgyleMiddlesbrough 0-2 Plymouth Argyle | Sky Bet Championship |
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