| 1 | Fri 7 Aug | 191-0 v WrexhamMiddlesbrough 1-0 Wrexham | Carabao Cup First Round |
| 2 | Sat 15 Aug | 192-1 v Lincoln CityMiddlesbrough 2-1 Lincoln City | Sky Bet Championship |
| 3 | Sat 22 Aug | 191-2 v Blackburn RoversBlackburn Rovers 2-1 Middlesbrough | Sky Bet Championship |
| 4 | Tue 25 Aug | 193-1 v Doncaster RoversDoncaster Rovers 1-3 Middlesbrough | Carabao Cup Second Round |
| 5 | Wed 2 Sep | 191-1 v BurnleyBurnley 1-1 Middlesbrough | Sky Bet Championship |
| 6 | Tue 8 Sep | 190-3 v Crystal PalaceCrystal Palace 3-0 Middlesbrough | Carabao Cup Third Round |
| 7 | Fri 23 Oct | 195-1 v Bolton WanderersBolton Wanderers 1-5 Middlesbrough | Sky Bet Championship |
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