| 1 | Sat 9 Aug | 21-0 v Swansea CityMiddlesbrough 1-0 Swansea City | Sky Bet Championship |
| 2 | Tue 12 Aug | 20-4 v Doncaster RoversMiddlesbrough 0-4 Doncaster Rovers | Carabao Cup First Round |
| 3 | Sat 16 Aug | 23-0 v MillwallMillwall 0-3 Middlesbrough | Sky Bet Championship |
| 4 | Sat 23 Aug | 2 2-1 v Norwich CityNorwich City 1-2 Middlesbrough | Sky Bet Championship |
| 5 | Sat 30 Aug | 21-0 v Sheffield UnitedMiddlesbrough 1-0 Sheffield United | Sky Bet Championship |
| 6 | Sat 13 Sep | 22-2 v Preston North EndPreston North End 2-2 Middlesbrough | Sky Bet Championship |
| 7 | Fri 19 Sep | 22-1 v West Bromwich AlbionMiddlesbrough 2-1 West Bromwich Albion | Sky Bet Championship |
| 8 | Sat 27 Sep | 21-1 v SouthamptonSouthampton 1-1 Middlesbrough | Sky Bet Championship |
| 9 | Sat 4 Oct | 2 0-1 v PortsmouthPortsmouth 1-0 Middlesbrough | Sky Bet Championship |
| 10 | Fri 17 Oct | 2 2-1 v Ipswich TownMiddlesbrough 2-1 Ipswich Town | Sky Bet Championship |
| 11 | Wed 22 Oct | 21-0 v Sheffield WednesdaySheffield Wednesday 0-1 Middlesbrough | Sky Bet Championship |
| 12 | Sat 25 Oct | 21-1 v WrexhamMiddlesbrough 1-1 Wrexham | Sky Bet Championship |
| 13 | Sat 1 Nov | 20-3 v WatfordWatford 3-0 Middlesbrough | Sky Bet Championship |
| 14 | Tue 4 Nov | 2 1-1 v Leicester CityLeicester City 1-1 Middlesbrough | Sky Bet Championship |
| 15 | Sat 8 Nov | 22-1 v Birmingham CityMiddlesbrough 2-1 Birmingham City | Sky Bet Championship |
| 16 | Sat 22 Nov | 21-1 v Oxford UnitedOxford United 1-1 Middlesbrough | Sky Bet Championship |
| 17 | Tue 25 Nov | 22-4 v Coventry CityMiddlesbrough 2-4 Coventry City | Sky Bet Championship |
| 18 | Sat 29 Nov | 22-1 v Derby CountyMiddlesbrough 2-1 Derby County | Sky Bet Championship |
| 19 | Fri 5 Dec | 24-1 v Hull CityHull City 1-4 Middlesbrough | Sky Bet Championship |
| 20 | Tue 9 Dec | 22-1 v Charlton AthleticCharlton Athletic 1-2 Middlesbrough | Sky Bet Championship |
| 21 | Sat 13 Dec | 23-1 v Queens Park RangersMiddlesbrough 3-1 Queens Park Rangers | Sky Bet Championship |
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