| 2. Ronde | 17.08.2019 | FC Helsingør [B-jun] | - | B.93 København [B-jun] | 1:2 | ||||
| 3. Ronde | 24.08.2019 | AC Horsens [B-jun] | - | FC Helsingør [B-jun] | 5:3 | ||||
| 5. Ronde | 07.09.2019 | Kolding IF [B-jun] | - | FC Helsingør [B-jun] | 6:2 |  |
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| 6. Ronde | 14.09.2019 | FC Helsingør [B-jun] | - | Hellerup IK [B-jun] | 1:0 | ||||
| 7. Ronde | 21.09.2019 | FC Helsingør [B-jun] | - | Viborg FF [B-jun] | 5:2 | ||||
| 8. Ronde | 28.09.2019 | FC Roskilde [B-jun] | - | FC Helsingør [B-jun] | 5:2 | |
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| 11. Ronde | 19.10.2019 | FC Helsingør [B-jun] | - | Næstved BK [B-jun] | 8:0 | ||||
| 12. Ronde | 26.10.2019 | HB Køge [B-jun] | - | FC Helsingør [B-jun] | 0:0 | ||||
| 13. Ronde | 02.11.2019 | FC Helsingør [B-jun] | - | Næsby BK [B-jun] | 2:1 | |
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| 14. Ronde | 09.11.2019 | AB Gladsaxe [B-jun] | - | FC Helsingør [B-jun] | 4:2 | ||||
| 4. Ronde | 30.11.2019 | FC Helsingør [B-jun] | - | Hobro IK [B-jun] | 4:1 |
Denemarken