| 2. Ronde | 21.09.2020 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 | ||||
| 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 | ||||
| 8. Ronde | 08.11.2020 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 0:1 | ||||
| 15. Ronde | 25.01.2021 | Stoke City U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 18. Ronde | 15.02.2021 | Middlesbrough FC U23 | - | Sunderland AFC U23 | 1:1 |  |
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| 19. Ronde | 22.02.2021 | Burnley FC U23 | - | Middlesbrough FC U23 | 3:2 | |
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| 20. Ronde | 26.02.2021 | Middlesbrough FC U23 | - | Norwich City U23 | 0:3 | ||||
| 22. Ronde | 22.03.2021 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 1:1 |  |
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| 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 | ||||
| 25. Ronde | 23.04.2021 | Middlesbrough FC U23 | - | Aston Villa U23 | 4:1 |
Nigeria