| 2. Round | 18/08/2018 | Middlesbrough FC [U18] | - | Stoke City [U18] | 2:0 |  |
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| 3. Round | 25/08/2018 | Everton FC [U18] | - | Middlesbrough FC [U18] | 2:1 | ||||
| 4. Round | 01/09/2018 | Middlesbrough FC [U18] | - | Manchester United [U18] | 3:1 | |
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| 6. Round | 22/09/2018 | Middlesbrough FC [U18] | - | Sunderland AFC [U18] | 1:1 | ||||
| 7. Round | 06/10/2018 | Wolverhampton Wanderers [U18] | - | Middlesbrough FC [U18] | 4:0 | |
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| 1. Round | 27/10/2018 | West Bromwich Albion [U18] | - | Middlesbrough FC [U18] | 1:2 | |
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| 10. Round | 24/11/2018 | Newcastle United [U18] | - | Middlesbrough FC [U18] | 2:3 |
England