| 1 | Thu 5 Jul 2018 | 40-1 v Sturm GrazSturm Graz 1-0 Middlesbrough | Friendly |
| 2 | Wed 18 Jul 2018 | 1-2 v FC AugsburgFC Augsburg 2-1 Middlesbrough | Friendly |
| 3 | Sat 21 Jul 2018 | 3-4 v Accrington StanleyAccrington Stanley 4-3 Middlesbrough | Friendly |
| 4 | Tue 7 Aug 2018 | 173-0 v Sheffield UnitedMiddlesbrough 3-0 Sheffield United | Sky Bet Championship |
| 5 | Sat 11 Aug 2018 | 171-0 v Birmingham CityMiddlesbrough 1-0 Birmingham City | Sky Bet Championship |
| 6 | Tue 14 Aug 2018 | 173-3 v Notts CountyMiddlesbrough 3-3 Notts County | Carabao Cup First Round |
| 7 | Sat 18 Aug 2018 | 172-0 v Bristol CityBristol City 0-2 Middlesbrough | Sky Bet Championship |
| 8 | Fri 24 Aug 2018 | 171-0 v West Bromwich AlbionMiddlesbrough 1-0 West Bromwich Albion | Sky Bet Championship |
| 9 | Tue 28 Aug 2018 | 172-1 v RochdaleMiddlesbrough 2-1 Rochdale | Carabao Cup Second Round |
| 10 | Tue 25 Sep 2018 | 172-2 v Preston North EndPreston North End 2-2 Middlesbrough | Carabao Cup Third Round |
| 11 | Tue 2 Oct 2018 | 172-0 v Ipswich TownIpswich Town 0-2 Middlesbrough | Sky Bet Championship |
| 12 | Tue 23 Oct 2018 | 170-0 v Rotherham UnitedMiddlesbrough 0-0 Rotherham United | Sky Bet Championship |
| 13 | Sat 27 Oct 2018 | 171-1 v Derby CountyMiddlesbrough 1-1 Derby County | Sky Bet Championship |
| 14 | Wed 31 Oct 2018 | 171-0 v Crystal PalaceMiddlesbrough 1-0 Crystal Palace | Carabao Cup Fourth Round |
| 15 | Sat 1 Dec 2018 | 170-3 v Aston VillaMiddlesbrough 0-3 Aston Villa | Sky Bet Championship |
| 16 | Sat 22 Dec 2018 | 171-0 v ReadingReading 0-1 Middlesbrough | Sky Bet Championship |
| 17 | Wed 26 Dec 2018 | 17 0-1 v Sheffield WednesdayMiddlesbrough 0-1 Sheffield Wednesday | Sky Bet Championship |
| 18 | Tue 1 Jan 2019 | 171-1 v Derby CountyDerby County 1-1 Middlesbrough | Sky Bet Championship |
| 19 | Sat 5 Jan 2019 | 175-0 v Peterborough UnitedMiddlesbrough 5-0 Peterborough United | Emirates FA Cup Third Round |
| 20 | Sat 12 Jan 2019 | 172-1 v Birmingham CityBirmingham City 1-2 Middlesbrough | Sky Bet Championship |
| 21 | Sat 26 Jan 2019 | 171-1 v Newport CountyMiddlesbrough 1-1 Newport County | Emirates FA Cup Fourth Round |
| 22 | Tue 5 Feb 2019 | 170-2 v Newport CountyNewport County 2-0 Middlesbrough | Emirates FA Cup Fourth Round |
| 23 | Sun 17 Feb 2019 | 171-0 v Blackburn RoversBlackburn Rovers 0-1 Middlesbrough | Sky Bet Championship |
| 24 | Fri 19 Apr 2019 | 171-0 v Stoke CityMiddlesbrough 1-0 Stoke City | Sky Bet Championship |
| 25 | Mon 22 Apr 2019 | 170-3 v Nottingham ForestNottingham Forest 3-0 Middlesbrough | Sky Bet Championship |
| 26 | Sat 27 Apr 2019 | 172-1 v ReadingMiddlesbrough 2-1 Reading | Sky Bet Championship |
| 27 | Sun 5 May 2019 | 172-1 v Rotherham UnitedRotherham United 1-2 Middlesbrough | Sky Bet Championship |
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