| 1. Round | 10/08/2019 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 3:3 | ||||
| 3. Round | 24/08/2019 | Middlesbrough FC [U18] | - | Manchester City [U18] | 1:3 |  |
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| 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 | ||||
| 6. Round | 21/09/2019 | Liverpool FC [U18] | - | Middlesbrough FC [U18] | 3:0 | ||||
| 7. Round | 05/10/2019 | Middlesbrough FC [U18] | - | Stoke City [U18] | 1:1 | ||||
| 8. Round | 19/10/2019 | Manchester United [U18] | - | Middlesbrough FC [U18] | 1:1 | ||||
| 9. Round | 02/11/2019 | Middlesbrough FC [U18] | - | Sunderland AFC [U18] | 4:3 | |
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| 11. Round | 06/12/2019 | Middlesbrough FC [U18] | - | West Bromwich Albion [U18] | 3:2 |
England