| 1. Ronde | 11.09.2020 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 | ||||
| 2. Ronde | 21.09.2020 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 |  |
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| 5. Ronde | 19.10.2020 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 0:6 | ||||
| 18. Ronde | 15.02.2021 | Middlesbrough FC U23 | - | Sunderland AFC U23 | 1:1 | ||||
| 19. Ronde | 22.02.2021 | Burnley FC U23 | - | Middlesbrough FC U23 | 3:2 | |
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| 21. Ronde | 12.03.2021 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 0:1 | |
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| 22. Ronde | 22.03.2021 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 1:1 | ||||
| 23. Ronde | 09.04.2021 | Reading FC U23 | - | Middlesbrough FC U23 | 2:4 | |
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| 24. Ronde | 16.04.2021 | Middlesbrough FC U23 | - | Fulham FC U23 | 1:0 |  |
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| 25. Ronde | 23.04.2021 | Middlesbrough FC U23 | - | Aston Villa U23 | 4:1 |
Engeland