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