2. Round | 18/08/2018 | Middlesbrough FC [U18] | - | Stoke City [U18] | 2:0 | ||||
4. Round | 01/09/2018 | Middlesbrough FC [U18] | - | Manchester United [U18] | 3:1 | ||||
5. Round | 15/09/2018 | Derby County [U18] | - | Middlesbrough FC [U18] | 3:2 | ||||
10. Round | 24/11/2018 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 2:3 | ||||
11. Round | 01/12/2018 | Middlesbrough FC [U18] | - | Liverpool FC [U18] | 5:6 | ||||
9. Round | 04/12/2018 | Manchester City [U18] | - | Middlesbrough FC [U18] | 6:0 | ||||
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 | ||||
20. Round | 06/04/2019 | Blackburn Rovers [U18] | - | Middlesbrough FC [U18] | 3:1 | ||||
21. Round | 13/04/2019 | Middlesbrough FC [U18] | - | Newcastle United [U18] | 4:1 |