| 1 | Wed 18 Jul 2018 | 181-2 v FC AugsburgFC Augsburg 2-1 Middlesbrough | Friendly |
| 2 | Tue 24 Jul 2018 | 182-3 v RochdaleRochdale 3-2 Middlesbrough | Friendly |
| 3 | Tue 7 Aug 2018 | 183-0 v Sheffield UnitedMiddlesbrough 3-0 Sheffield United | Sky Bet Championship |
| 4 | Sat 11 Aug 2018 | 181-0 v Birmingham CityMiddlesbrough 1-0 Birmingham City | Sky Bet Championship |
| 5 | Tue 14 Aug 2018 | 183-3 v Notts CountyMiddlesbrough 3-3 Notts County | Carabao Cup First Round |
| 6 | Sat 18 Aug 2018 | 182-0 v Bristol CityBristol City 0-2 Middlesbrough | Sky Bet Championship |
| 7 | Fri 24 Aug 2018 | 18 1-0 v West Bromwich AlbionMiddlesbrough 1-0 West Bromwich Albion | Sky Bet Championship |
| 8 | Tue 28 Aug 2018 | 182-1 v RochdaleMiddlesbrough 2-1 Rochdale | Carabao Cup Second Round |
| 9 | Tue 25 Sep 2018 | 182-2 v Preston North EndPreston North End 2-2 Middlesbrough | Carabao Cup Third Round |
| 10 | Wed 31 Oct 2018 | 181-0 v Crystal PalaceMiddlesbrough 1-0 Crystal Palace | Carabao Cup Fourth Round |
| 11 | Sat 8 Dec 2018 | 181-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 12 | Sat 15 Dec 2018 | 181-2 v Queens Park RangersQueens Park Rangers 2-1 Middlesbrough | Sky Bet Championship |
| 13 | Tue 18 Dec 2018 | 180-1 v Burton AlbionMiddlesbrough 0-1 Burton Albion | Carabao Cup Quarter Final |
| 14 | Sat 5 Jan 2019 | 185-0 v Peterborough UnitedMiddlesbrough 5-0 Peterborough United | Emirates FA Cup Third Round |
| 15 | Sat 26 Jan 2019 | 18 1-1 v Newport CountyMiddlesbrough 1-1 Newport County | Emirates FA Cup Fourth Round |
| 16 | Tue 5 Feb 2019 | 180-2 v Newport CountyNewport County 2-0 Middlesbrough | Emirates FA Cup Fourth Round |
| 17 | Sun 17 Feb 2019 | 181-0 v Blackburn RoversBlackburn Rovers 0-1 Middlesbrough | Sky Bet Championship |
| 18 | Sat 23 Feb 2019 | 182-0 v Queens Park RangersMiddlesbrough 2-0 Queens Park Rangers | Sky Bet Championship |
| 19 | Sat 2 Mar 2019 | 180-0 v Wigan AthleticWigan Athletic 0-0 Middlesbrough | Sky Bet Championship |
| 20 | Sat 9 Mar 2019 | 181-2 v BrentfordMiddlesbrough 1-2 Brentford | Sky Bet Championship |
| 21 | Wed 13 Mar 2019 | 181-2 v Preston North EndMiddlesbrough 1-2 Preston North End | Sky Bet Championship |
| 22 | Sat 16 Mar 2019 | 180-3 v Aston VillaAston Villa 3-0 Middlesbrough | Sky Bet Championship |
| 23 | Sat 30 Mar 2019 | 180-1 v Norwich CityMiddlesbrough 0-1 Norwich City | Sky Bet Championship |
| 24 | Tue 2 Apr 2019 | 180-1 v Bristol CityMiddlesbrough 0-1 Bristol City | Sky Bet Championship |
| 25 | Sat 6 Apr 2019 | 181-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
| 26 | Tue 9 Apr 2019 | 182-0 v Bolton WanderersBolton Wanderers 0-2 Middlesbrough | Sky Bet Championship |
| 27 | Sat 13 Apr 2019 | 181-0 v Hull CityMiddlesbrough 1-0 Hull City | Sky Bet Championship |
| 28 | Fri 19 Apr 2019 | 181-0 v Stoke CityMiddlesbrough 1-0 Stoke City | Sky Bet Championship |
| 29 | Mon 22 Apr 2019 | 180-3 v Nottingham ForestNottingham Forest 3-0 Middlesbrough | Sky Bet Championship |
| 30 | Sat 27 Apr 2019 | 182-1 v ReadingMiddlesbrough 2-1 Reading | Sky Bet Championship |
| 31 | Sun 5 May 2019 | 182-1 v Rotherham UnitedRotherham United 1-2 Middlesbrough | Sky Bet Championship |
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