| 1 | Fri 7 Aug | 21-0 v WrexhamMiddlesbrough 1-0 Wrexham | Carabao Cup First Round |
| 2 | Sat 15 Aug | 22-1 v Lincoln CityMiddlesbrough 2-1 Lincoln City | Sky Bet Championship |
| 3 | Sat 22 Aug | 21-2 v Blackburn RoversBlackburn Rovers 2-1 Middlesbrough | Sky Bet Championship |
| 4 | Tue 25 Aug | 23-1 v Doncaster RoversDoncaster Rovers 1-3 Middlesbrough | Carabao Cup Second Round |
| 5 | Sat 29 Aug | 23-1 v West Bromwich AlbionMiddlesbrough 3-1 West Bromwich Albion | Sky Bet Championship |
| 6 | Wed 2 Sep | 21-1 v BurnleyBurnley 1-1 Middlesbrough | Sky Bet Championship |
| 7 | Sat 5 Sep | 2 1-0 v Queens Park RangersQueens Park Rangers 0-1 Middlesbrough | Sky Bet Championship |
| 8 | Tue 8 Sep | 20-3 v Crystal PalaceCrystal Palace 3-0 Middlesbrough | Carabao Cup Third Round |
| 9 | Sat 12 Sep | 24-3 v Norwich CityMiddlesbrough 4-3 Norwich City | Sky Bet Championship |
| 10 | Tue 15 Sep | 22-2 v MillwallMiddlesbrough 2-2 Millwall | Sky Bet Championship |
| 11 | Sat 19 Sep | 22-2 v Birmingham CityBirmingham City 2-2 Middlesbrough | Sky Bet Championship |
| 12 | Sat 10 Oct | 21-0 v Wolverhampton WanderersMiddlesbrough 1-0 Wolverhampton Wanderers | Sky Bet Championship |
| 13 | Tue 13 Oct | 23-2 v Stoke CityStoke City 2-3 Middlesbrough | Sky Bet Championship |
| 14 | Sat 17 Oct | 22-2 v Cardiff CityMiddlesbrough 2-2 Cardiff City | Sky Bet Championship |
| 15 | Fri 23 Oct | 25-1 v Bolton WanderersBolton Wanderers 1-5 Middlesbrough | Sky Bet Championship |
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