| 5. Ronde | 07.09.2019 | Kolding IF [A-jun] | - | FC Helsingør [A-jun] | 0:1 | ||||
| 6. Ronde | 14.09.2019 | FC Helsingør [A-jun] | - | Hellerup IK [A-jun] | 7:0 | ||||
| 8. Ronde | 28.09.2019 | FC Roskilde [A-jun] | - | FC Helsingør [A-jun] | 1:3 | ||||
| 9. Ronde | 05.10.2019 | FC Helsingør [A-jun] | - | Hvidovre IF [A-jun] | 1:0 | ||||
| 12. Ronde | 26.10.2019 | HB Køge [A-jun] | - | FC Helsingør [A-jun] | 5:1 | ||||
| 14. Ronde | 09.11.2019 | AB Gladsaxe [A-jun] | - | FC Helsingør [A-jun] | 1:3 | ||||
| 15. Ronde | 16.11.2019 | FC Helsingør [A-jun] | - | Holbæk B&I [A-jun] | 4:0 |
Denemarken