| 1 | Tue 13 Aug 2019 | 32-2 v Crewe AlexandraMiddlesbrough 2-2 Crewe Alexandra | Carabao Cup First Round |
| 2 | Sat 17 Aug 2019 | 30-1 v Blackburn RoversBlackburn Rovers 1-0 Middlesbrough | Sky Bet Championship |
| 3 | Sat 9 Nov 2019 | 32-2 v Queens Park RangersQueens Park Rangers 2-2 Middlesbrough | Sky Bet Championship |
| 4 | Sat 15 Feb 2020 | 30-1 v Luton TownMiddlesbrough 0-1 Luton Town | Sky Bet Championship |
| 5 | Sat 22 Feb 2020 | 30-1 v BarnsleyBarnsley 1-0 Middlesbrough | Sky Bet Championship |
| 6 | Wed 26 Feb 2020 | 30-1 v Leeds UnitedMiddlesbrough 0-1 Leeds United | Sky Bet Championship |
| 7 | Sat 20 Jun 2020 | 30-3 v Swansea CityMiddlesbrough 0-3 Swansea City | Sky Bet Championship |
| 8 | Sat 27 Jun 2020 | 32-0 v Stoke CityStoke City 0-2 Middlesbrough | Sky Bet Championship |
| 9 | Thu 2 Jul 2020 | 31-2 v Hull CityHull City 2-1 Middlesbrough | Sky Bet Championship |
| 10 | Sun 5 Jul 2020 | 30-1 v Queens Park RangersMiddlesbrough 0-1 Queens Park Rangers | Sky Bet Championship |
| 11 | Wed 8 Jul 2020 | 32-0 v MillwallMillwall 0-2 Middlesbrough | Sky Bet Championship |
| 12 | Sat 11 Jul 2020 | 31-3 v Bristol CityMiddlesbrough 1-3 Bristol City | Sky Bet Championship |
| 13 | Tue 14 Jul 2020 | 32-1 v ReadingReading 1-2 Middlesbrough | Sky Bet Championship |
| 14 | Sat 18 Jul 2020 | 3 1-3 v Cardiff CityMiddlesbrough 1-3 Cardiff City | Sky Bet Championship |
| 15 | Wed 22 Jul 2020 | 32-1 v Sheffield WednesdaySheffield Wednesday 1-2 Middlesbrough | Sky Bet Championship |
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