| 2. Round | 18/08/2018 | FC Helsingør [Youth B] | - | Hellerup IK [Youth B] | 0:2 | ||||
| 3. Round | 25/08/2018 | AC Horsens [Youth B] | - | FC Helsingør [Youth B] | 3:1 | ||||
| 5. Round | 08/09/2018 | Viborg FF [Youth B] | - | FC Helsingør [Youth B] | 3:3 | ||||
| 6. Round | 15/09/2018 | FC Helsingør [Youth B] | - | Hvidovre IF [Youth B] | 1:3 |  |
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| 7. Round | 22/09/2018 | Næstved BK [Youth B] | - | FC Helsingør [Youth B] | 1:2 | ||||
| 9. Round | 06/10/2018 | B.93 København [Youth B] | - | FC Helsingør [Youth B] | 8:1 | ||||
| 10. Round | 13/10/2018 | FC Helsingør [Youth B] | - | Thisted FC [Youth B] | 2:1 | |
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| 11. Round | 27/10/2018 | Slagelse B&I [Youth B] | - | FC Helsingør [Youth B] | 2:1 | ||||
| 4. Round | 02/03/2019 | FC Helsingør [Youth B] | - | Næsby BK [Youth B] | 3:2 |  |
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| 18. Round | 30/03/2019 | FC Helsingør [Youth B] | - | Viborg FF [Youth B] | 1:8 | ||||
| 19. Round | 06/04/2019 | Hvidovre IF [Youth B] | - | FC Helsingør [Youth B] | 0:1 |  |
Denmark