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 | ||||
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 | ||||
10. Round | 25/01/2020 | Blackburn Rovers [U18] | - | Middlesbrough FC [U18] | 2:3 |