| 1 | Sat 5 Aug | 16 0-1 v MillwallMiddlesbrough 0-1 Millwall | Sky Bet Championship |
| 2 | Sat 12 Aug | 160-3 v Coventry CityCoventry City 3-0 Middlesbrough | Sky Bet Championship |
| 3 | Sat 19 Aug | 16 1-1 v Huddersfield TownMiddlesbrough 1-1 Huddersfield Town | Sky Bet Championship |
| 4 | Sat 26 Aug | 162-4 v West Bromwich AlbionWest Bromwich Albion 4-2 Middlesbrough | Sky Bet Championship |
| 5 | Sat 2 Sep | 160-2 v Queens Park RangersMiddlesbrough 0-2 Queens Park Rangers | Sky Bet Championship |
| 6 | Sat 16 Sep | 161-2 v Blackburn RoversBlackburn Rovers 2-1 Middlesbrough | Sky Bet Championship |
| 7 | Sat 23 Sep | 162-1 v SouthamptonMiddlesbrough 2-1 Southampton | Sky Bet Championship |
| 8 | Sat 30 Sep | 163-2 v WatfordWatford 2-3 Middlesbrough | Sky Bet Championship |
| 9 | Sat 21 Oct | 161-0 v Birmingham CityMiddlesbrough 1-0 Birmingham City | Sky Bet Championship |
| 10 | Tue 24 Oct | 162-1 v Norwich CityNorwich City 1-2 Middlesbrough | Sky Bet Championship |
| 11 | Sat 28 Oct | 160-2 v Stoke CityMiddlesbrough 0-2 Stoke City | Sky Bet Championship |
| 12 | Sat 4 Nov | 163-3 v Plymouth ArgylePlymouth Argyle 3-3 Middlesbrough | Sky Bet Championship |
| 13 | Sat 11 Nov | 16 1-0 v Leicester CityMiddlesbrough 1-0 Leicester City | Sky Bet Championship |
| 14 | Sat 25 Nov | 162-3 v Bristol CityBristol City 3-2 Middlesbrough | Sky Bet Championship |
| 15 | Tue 28 Nov | 164-0 v Preston North EndMiddlesbrough 4-0 Preston North End | Sky Bet Championship |
| 16 | Sat 2 Dec | 16 2-3 v Leeds UnitedLeeds United 3-2 Middlesbrough | Sky Bet Championship |
| 17 | Sat 9 Dec | 160-2 v Ipswich TownMiddlesbrough 0-2 Ipswich Town | Sky Bet Championship |
| 18 | Wed 13 Dec | 161-2 v Hull CityMiddlesbrough 1-2 Hull City | Sky Bet Championship |
| 19 | Sat 16 Dec | 16 2-1 v Swansea CitySwansea City 1-2 Middlesbrough | Sky Bet Championship |
| 20 | Tue 19 Dec | 163-0 v Port ValePort Vale 0-3 Middlesbrough | Carabao Cup Quarter Final |
| 21 | Sat 23 Dec | 16 1-0 v West Bromwich AlbionMiddlesbrough 1-0 West Bromwich Albion | Sky Bet Championship |
| 22 | Tue 26 Dec | 160-1 v Rotherham UnitedRotherham United 1-0 Middlesbrough | Sky Bet Championship |
| 23 | Fri 29 Dec | 162-1 v Huddersfield TownHuddersfield Town 1-2 Middlesbrough | Sky Bet Championship |
| 24 | Mon 1 Jan | 161-3 v Coventry CityMiddlesbrough 1-3 Coventry City | Sky Bet Championship |
| 25 | Sat 6 Jan | 160-1 v Aston VillaMiddlesbrough 0-1 Aston Villa | Emirates FA Cup Third Round |
| 26 | Tue 9 Jan | 161-0 v ChelseaMiddlesbrough 1-0 Chelsea | Carabao Cup Semi Final |
| 27 | Sat 13 Jan | 163-1 v MillwallMillwall 1-3 Middlesbrough | Sky Bet Championship |
| 28 | Tue 23 Jan | 161-6 v ChelseaChelsea 6-1 Middlesbrough | Carabao Cup Semi Final |
| 29 | Sun 4 Feb | 161-1 v SunderlandMiddlesbrough 1-1 Sunderland | Sky Bet Championship |
| 30 | Wed 14 Feb | 161-2 v Preston North EndPreston North End 2-1 Middlesbrough | Sky Bet Championship |
| 31 | Wed 6 Mar | 163-1 v Norwich CityMiddlesbrough 3-1 Norwich City | Sky Bet Championship |
| 32 | Sat 9 Mar | 162-0 v Queens Park RangersQueens Park Rangers 0-2 Middlesbrough | Sky Bet Championship |
| 33 | Tue 12 Mar | 16 1-0 v Birmingham CityBirmingham City 0-1 Middlesbrough | Sky Bet Championship |
| 34 | Sat 16 Mar | 160-0 v Blackburn RoversMiddlesbrough 0-0 Blackburn Rovers | Sky Bet Championship |
| 35 | Fri 29 Mar | 161-1 v SouthamptonSouthampton 1-1 Middlesbrough | Sky Bet Championship |
| 36 | Mon 1 Apr | 162-0 v Sheffield WednesdayMiddlesbrough 2-0 Sheffield Wednesday | Sky Bet Championship |
| 37 | Sat 6 Apr | 162-0 v Swansea CityMiddlesbrough 2-0 Swansea City | Sky Bet Championship |
| 38 | Wed 10 Apr | 162-2 v Hull CityHull City 2-2 Middlesbrough | Sky Bet Championship |
| 39 | Sat 13 Apr | 16 1-1 v Ipswich TownIpswich Town 1-1 Middlesbrough | Sky Bet Championship |
| 40 | Mon 22 Apr | 16 3-4 v Leeds UnitedMiddlesbrough 3-4 Leeds United | Sky Bet Championship |
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