| 1 | Thu 5 Jul 2018 | 200-1 v Sturm GrazSturm Graz 1-0 Middlesbrough | Friendly |
| 2 | Wed 18 Jul 2018 | 201-2 v FC AugsburgFC Augsburg 2-1 Middlesbrough | Friendly |
| 3 | Tue 24 Jul 2018 | 202-3 v RochdaleRochdale 3-2 Middlesbrough | Friendly |
| 4 | Sat 4 Aug 2018 | 202-2 v MillwallMillwall 2-2 Middlesbrough | Sky Bet Championship |
| 5 | Tue 7 Aug 2018 | 203-0 v Sheffield UnitedMiddlesbrough 3-0 Sheffield United | Sky Bet Championship |
| 6 | Sat 11 Aug 2018 | 201-0 v Birmingham CityMiddlesbrough 1-0 Birmingham City | Sky Bet Championship |
| 7 | Tue 14 Aug 2018 | 203-3 v Notts CountyMiddlesbrough 3-3 Notts County | Carabao Cup First Round |
| 8 | Sat 18 Aug 2018 | 20 2-0 v Bristol CityBristol City 0-2 Middlesbrough | Sky Bet Championship |
| 9 | Fri 24 Aug 2018 | 201-0 v West Bromwich AlbionMiddlesbrough 1-0 West Bromwich Albion | Sky Bet Championship |
| 10 | Fri 31 Aug 2018 | 200-0 v Leeds UnitedLeeds United 0-0 Middlesbrough | Sky Bet Championship |
| 11 | Sat 15 Sep 2018 | 200-1 v Norwich CityNorwich City 1-0 Middlesbrough | Sky Bet Championship |
| 12 | Tue 25 Sep 2018 | 202-2 v Preston North EndPreston North End 2-2 Middlesbrough | Carabao Cup Third Round |
| 13 | Fri 19 Oct 2018 | 202-1 v Sheffield WednesdaySheffield Wednesday 1-2 Middlesbrough | Sky Bet Championship |
| 14 | Sat 27 Oct 2018 | 201-1 v Derby CountyMiddlesbrough 1-1 Derby County | Sky Bet Championship |
| 15 | Sat 3 Nov 2018 | 200-0 v Stoke CityStoke City 0-0 Middlesbrough | Sky Bet Championship |
| 16 | Sat 10 Nov 2018 | 202-0 v Wigan AthleticMiddlesbrough 2-0 Wigan Athletic | Sky Bet Championship |
| 17 | Sat 24 Nov 2018 | 202-1 v BrentfordBrentford 1-2 Middlesbrough | Sky Bet Championship |
| 18 | Tue 27 Nov 2018 | 201-1 v Preston North EndPreston North End 1-1 Middlesbrough | Sky Bet Championship |
| 19 | Sat 1 Dec 2018 | 200-3 v Aston VillaMiddlesbrough 0-3 Aston Villa | Sky Bet Championship |
| 20 | Tue 18 Dec 2018 | 200-1 v Burton AlbionMiddlesbrough 0-1 Burton Albion | Carabao Cup Quarter Final |
| 21 | Sat 22 Dec 2018 | 201-0 v ReadingReading 0-1 Middlesbrough | Sky Bet Championship |
| 22 | Wed 26 Dec 2018 | 200-1 v Sheffield WednesdayMiddlesbrough 0-1 Sheffield Wednesday | Sky Bet Championship |
| 23 | Sat 29 Dec 2018 | 202-0 v Ipswich TownMiddlesbrough 2-0 Ipswich Town | Sky Bet Championship |
| 24 | Tue 1 Jan 2019 | 201-1 v Derby CountyDerby County 1-1 Middlesbrough | Sky Bet Championship |
| 25 | Sat 5 Jan 2019 | 205-0 v Peterborough UnitedMiddlesbrough 5-0 Peterborough United | Emirates FA Cup Third Round |
| 26 | Sat 12 Jan 2019 | 202-1 v Birmingham CityBirmingham City 1-2 Middlesbrough | Sky Bet Championship |
| 27 | Sat 19 Jan 2019 | 201-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 28 | Sat 2 Feb 2019 | 203-2 v West Bromwich AlbionWest Bromwich Albion 2-3 Middlesbrough | Sky Bet Championship |
| 29 | Tue 5 Feb 2019 | 200-2 v Newport CountyNewport County 2-0 Middlesbrough | Emirates FA Cup Fourth Round |
| 30 | Sat 9 Feb 2019 | 201-1 v Leeds UnitedMiddlesbrough 1-1 Leeds United | Sky Bet Championship |
| 31 | Wed 13 Feb 2019 | 200-1 v Sheffield UnitedSheffield United 1-0 Middlesbrough | Sky Bet Championship |
| 32 | Sun 17 Feb 2019 | 201-0 v Blackburn RoversBlackburn Rovers 0-1 Middlesbrough | Sky Bet Championship |
| 33 | Sat 23 Feb 2019 | 202-0 v Queens Park RangersMiddlesbrough 2-0 Queens Park Rangers | Sky Bet Championship |
| 34 | Sat 2 Mar 2019 | 200-0 v Wigan AthleticWigan Athletic 0-0 Middlesbrough | Sky Bet Championship |
| 35 | Sat 9 Mar 2019 | 201-2 v BrentfordMiddlesbrough 1-2 Brentford | Sky Bet Championship |
| 36 | Wed 13 Mar 2019 | 201-2 v Preston North EndMiddlesbrough 1-2 Preston North End | Sky Bet Championship |
| 37 | Sat 16 Mar 2019 | 200-3 v Aston VillaAston Villa 3-0 Middlesbrough | Sky Bet Championship |
| 38 | Sat 30 Mar 2019 | 200-1 v Norwich CityMiddlesbrough 0-1 Norwich City | Sky Bet Championship |
| 39 | Tue 2 Apr 2019 | 200-1 v Bristol CityMiddlesbrough 0-1 Bristol City | Sky Bet Championship |
| 40 | Sat 6 Apr 2019 | 201-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
| 41 | Tue 9 Apr 2019 | 202-0 v Bolton WanderersBolton Wanderers 0-2 Middlesbrough | Sky Bet Championship |
| 42 | Sat 13 Apr 2019 | 201-0 v Hull CityMiddlesbrough 1-0 Hull City | Sky Bet Championship |
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