| 1. Round | 10/08/2019 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 3:3 |  |
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| 3. Round | 24/08/2019 | Middlesbrough FC [U18] | - | Manchester City [U18] | 1:3 | ||||
| 4. Round | 31/08/2019 | Derby County [U18] | - | Middlesbrough FC [U18] | 4:1 | ||||
| 5. Round | 14/09/2019 | Middlesbrough FC [U18] | - | Wolverhampton Wanderers [U18] | 2:0 | ||||
| 7. Round | 05/10/2019 | Middlesbrough FC [U18] | - | Stoke City [U18] | 1:1 | ||||
| 13. Round | 11/01/2020 | Everton FC [U18] | - | Middlesbrough FC [U18] | 1:0 | ||||
| 14. Round | 18/01/2020 | Middlesbrough FC [U18] | - | Derby County [U18] | 0:2 | ||||
| 10. Round | 25/01/2020 | Blackburn Rovers [U18] | - | Middlesbrough FC [U18] | 2:3 | |
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| 15. Round | 01/02/2020 | Manchester City [U18] | - | Middlesbrough FC [U18] | 6:2 | |
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| 12. Round | 08/02/2020 | Middlesbrough FC [U18] | - | Newcastle United [U18] | 4:2 | |
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| 16. Round | 22/02/2020 | Wolverhampton Wanderers [U18] | - | Middlesbrough FC [U18] | 5:0 | ||||
| 17. Round | 29/02/2020 | Middlesbrough FC [U18] | - | Liverpool FC [U18] | 3:0 | |
Ireland