| 2. Ronde | 17.08.2019 | FC Helsingør [A-jun] | - | B.93 København [A-jun] | 4:1 |  |
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| 3. Ronde | 24.08.2019 | AC Horsens [A-jun] | - | FC Helsingør [A-jun] | 2:4 | |
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| 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 | ||||
| 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 | |
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| 15. Ronde | 16.11.2019 | FC Helsingør [A-jun] | - | Holbæk B&I [A-jun] | 4:0 | ||||
| 4. Ronde | 30.11.2019 | FC Helsingør [A-jun] | - | Hobro IK [A-jun] | 4:3 |
Denemarken