| 1. Ronde | 10.08.2019 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 3:3 |  |
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| 4. Ronde | 31.08.2019 | Derby County [U18] | - | Middlesbrough FC [U18] | 4:1 | ||||
| 5. Ronde | 14.09.2019 | Middlesbrough FC [U18] | - | Wolverhampton Wanderers [U18] | 2:0 | |
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| 6. Ronde | 21.09.2019 | Liverpool FC [U18] | - | Middlesbrough FC [U18] | 3:0 | ||||
| 7. Ronde | 05.10.2019 | Middlesbrough FC [U18] | - | Stoke City [U18] | 1:1 | |
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| 9. Ronde | 02.11.2019 | Middlesbrough FC [U18] | - | Sunderland AFC [U18] | 4:3 | ||||
| 12. Ronde | 08.02.2020 | Middlesbrough FC [U18] | - | Newcastle United [U18] | 4:2 | ||||
| 17. Ronde | 29.02.2020 | Middlesbrough FC [U18] | - | Liverpool FC [U18] | 3:0 |
Engeland