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| H (Match allé) | FC Zimbru | - | CS Petrocub | 1:2 | ||
| R (match retour) | CS Petrocub | - | FC Zimbru | 3:1 | ||
| H (Match allé): 24.09.2019 15:00 | R (match retour): 30.10.2019 16:30 | vainqueur: CS Petrocub | ||||
| H (Match allé) | FC Milsami | - | FC Sfîntul Gheorghe | 0:1 | ||
| R (match retour) | FC Sfîntul Gheorghe | - | FC Milsami | 0:0 | ||
| H (Match allé): 24.09.2019 18:00 | R (match retour): 30.10.2019 12:30 | vainqueur: FC Sfîntul Gheorghe | ||||
| H (Match allé) | FC Codru Lozova | - | Speranţa Nisporeni | 2:2 | ||
| R (match retour) | Speranţa Nisporeni | - | FC Codru Lozova | 5:0 | ||
| H (Match allé): 25.09.2019 15:00 | R (match retour): 29.10.2019 12:00 | vainqueur: Speranţa Nisporeni | ||||
| H (Match allé) | FC Sheriff | - | Dinamo-Auto | 1:0 | ||
| R (match retour) | Dinamo-Auto | - | FC Sheriff | 0:5 | ||
| H (Match allé): 25.09.2019 18:00 | R (match retour): 29.10.2019 12:00 | vainqueur: FC Sheriff | ||||
