3. Round | 25/08/2018 | Everton FC [U18] | - | Middlesbrough FC [U18] | 2:1 | ||||
5. Round | 15/09/2018 | Derby County [U18] | - | Middlesbrough FC [U18] | 3:2 | ||||
16. Round | 23/02/2019 | Middlesbrough FC [U18] | - | Derby County [U18] | 0:2 | ||||
17. Round | 02/03/2019 | Sunderland AFC [U18] | - | Middlesbrough FC [U18] | 2:8 | ||||
8. Round | 20/03/2019 | Middlesbrough FC [U18] | - | Blackburn Rovers [U18] | 2:2 | ||||
19. Round | 23/03/2019 | Middlesbrough FC [U18] | - | Manchester City [U18] | 4:2 | ||||
22. Round | 04/05/2019 | Liverpool FC [U18] | - | Middlesbrough FC [U18] | 1:0 |