| 1. Round | 11/09/2020 | Newcastle United U23 | - | Middlesbrough FC U23 | 2:2 | ||||
| 4. Round | 02/10/2020 | Leeds United U23 | - | Middlesbrough FC U23 | 1:0 | ||||
| 5. Round | 19/10/2020 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 0:6 | ||||
| 6. Round | 23/10/2020 | Middlesbrough FC U23 | - | Burnley FC U23 | 3:0 | ||||
| 7. Round | 30/10/2020 | Norwich City U23 | - | Middlesbrough FC U23 | 1:3 | ||||
| 8. Round | 08/11/2020 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 0:1 | ||||
| 9. Round | 20/11/2020 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 1:4 |  |
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| 10. Round | 27/11/2020 | Middlesbrough FC U23 | - | Reading FC U23 | 2:3 | |
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| 11. Round | 11/12/2020 | Fulham FC U23 | - | Middlesbrough FC U23 | 3:1 | |
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| 12. Round | 18/12/2020 | Aston Villa U23 | - | Middlesbrough FC U23 | 1:1 |
Spain
Northern Ireland