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 | ||||
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 | ||||
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 | ||||
11. Round | 06/12/2019 | Middlesbrough FC [U18] | - | West Bromwich Albion [U18] | 3:2 | ||||
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 | ||||
15. Round | 01/02/2020 | Manchester City [U18] | - | Middlesbrough FC [U18] | 6:2 | ||||
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 |