| 3. Round | 24/08/2019 | AC Horsens [Youth B] | - | FC Helsingør [Youth B] | 5:3 |  |
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| 5. Round | 07/09/2019 | Kolding IF [Youth B] | - | FC Helsingør [Youth B] | 6:2 | ||||
| 6. Round | 14/09/2019 | FC Helsingør [Youth B] | - | Hellerup IK [Youth B] | 1:0 | ||||
| 7. Round | 21/09/2019 | FC Helsingør [Youth B] | - | Viborg FF [Youth B] | 5:2 | ||||
| 8. Round | 28/09/2019 | FC Roskilde [Youth B] | - | FC Helsingør [Youth B] | 5:2 | ||||
| 9. Round | 05/10/2019 | FC Helsingør [Youth B] | - | Hvidovre IF [Youth B] | 7:2 | ||||
| 10. Round | 13/10/2019 | Slagelse B&I [Youth B] | - | FC Helsingør [Youth B] | 0:5 | |
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| 11. Round | 19/10/2019 | FC Helsingør [Youth B] | - | Næstved BK [Youth B] | 8:0 | |
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| 12. Round | 26/10/2019 | HB Køge [Youth B] | - | FC Helsingør [Youth B] | 0:0 | ||||
| 13. Round | 02/11/2019 | FC Helsingør [Youth B] | - | Næsby BK [Youth B] | 2:1 | ||||
| 14. Round | 09/11/2019 | AB Gladsaxe [Youth B] | - | FC Helsingør [Youth B] | 4:2 | ||||
| 15. Round | 16/11/2019 | FC Helsingør [Youth B] | - | Holbæk B&I [Youth B] | 3:1 | ||||
| 4. Round | 30/11/2019 | FC Helsingør [Youth B] | - | Hobro IK [Youth B] | 4:1 | |
Denmark