| 1. Ronde | 11.09.2020 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 |  |
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| 2. Ronde | 21.09.2020 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 | ||||
| 4. Ronde | 02.10.2020 | Leeds United U23 | - | Middlesbrough FC U23 | 1:0 | ||||
| 5. Ronde | 19.10.2020 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 0:6 | ||||
| 6. Ronde | 23.10.2020 | Middlesbrough FC U23 | - | Burnley FC U23 | 3:0 | ||||
| 7. Ronde | 30.10.2020 | Norwich City U23 | - | Middlesbrough FC U23 | 1:3 | ||||
| 8. Ronde | 08.11.2020 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 0:1 | ||||
| 9. Ronde | 20.11.2020 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 1:4 | ||||
| 10. Ronde | 27.11.2020 | Middlesbrough FC U23 | - | Reading FC U23 | 2:3 | ||||
| 15. Ronde | 25.01.2021 | Stoke City U23 | - | Middlesbrough FC U23 | 2:0 | |
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