| 2. Ronde | 18.08.2018 | Middlesbrough FC [U18] | - | Stoke City [U18] | 2:0 | ||||
| 3. Ronde | 25.08.2018 | Everton FC [U18] | - | Middlesbrough FC [U18] | 2:1 | ||||
| 4. Ronde | 01.09.2018 | Middlesbrough FC [U18] | - | Manchester United [U18] | 3:1 |  |
 |
||
| 6. Ronde | 22.09.2018 | Middlesbrough FC [U18] | - | Sunderland AFC [U18] | 1:1 | ||||
| 12. Ronde | 05.01.2019 | Stoke City [U18] | - | Middlesbrough FC [U18] | 3:1 | |
|||
| 13. Ronde | 12.01.2019 | Middlesbrough FC [U18] | - | West Bromwich Albion [U18] | 5:3 | |
|||
| 14. Ronde | 19.01.2019 | Middlesbrough FC [U18] | - | Everton FC [U18] | 3:2 | |
|||
| 15. Ronde | 02.02.2019 | Manchester United [U18] | - | Middlesbrough FC [U18] | 0:3 | ||||
| 8. Ronde | 20.03.2019 | Middlesbrough FC [U18] | - | Blackburn Rovers [U18] | 2:2 | ||||
| 19. Ronde | 23.03.2019 | Middlesbrough FC [U18] | - | Manchester City [U18] | 4:2 | ||||
| 21. Ronde | 13.04.2019 | Middlesbrough FC [U18] | - | Newcastle United [U18] | 4:1 | ||||
| 18. Ronde | 24.04.2019 | Middlesbrough FC [U18] | - | Wolverhampton Wanderers [U18] | 2:1 | ||||
| 22. Ronde | 04.05.2019 | Liverpool FC [U18] | - | Middlesbrough FC [U18] | 1:0 |
Engeland