| 1. Ronde | 09.08.2019 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:0 | ||||
| 2. Ronde | 16.08.2019 | Middlesbrough FC U23 | - | Stoke City U23 | 0:2 | ||||
| 3. Ronde | 23.08.2019 | Middlesbrough FC U23 | - | Swansea City U23 | 3:2 | ||||
| 4. Ronde | 30.08.2019 | Norwich City U23 | - | Middlesbrough FC U23 | 2:2 | ||||
| 9. Ronde | 28.10.2019 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 |
Engeland