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| 1st(1st leg) | FC Zimbru | - | CS Petrocub | 1:2 | ||
| 2nd (2nd leg) | CS Petrocub | - | FC Zimbru | 3:1 | ||
| 1st(1st leg): 24/09/2019 14:00 | 2nd (2nd leg): 30/10/2019 15:30 | Winner: CS Petrocub | ||||
| 1st(1st leg) | FC Milsami | - | FC Sfîntul Gheorghe | 0:1 | ||
| 2nd (2nd leg) | FC Sfîntul Gheorghe | - | FC Milsami | 0:0 | ||
| 1st(1st leg): 24/09/2019 17:00 | 2nd (2nd leg): 30/10/2019 11:30 | Winner: FC Sfîntul Gheorghe | ||||
| 1st(1st leg) | FC Codru Lozova | - | Speranţa Nisporeni | 2:2 | ||
| 2nd (2nd leg) | Speranţa Nisporeni | - | FC Codru Lozova | 5:0 | ||
| 1st(1st leg): 25/09/2019 14:00 | 2nd (2nd leg): 29/10/2019 11:00 | Winner: Speranţa Nisporeni | ||||
| 1st(1st leg) | FC Sheriff | - | Dinamo-Auto | 1:0 | ||
| 2nd (2nd leg) | Dinamo-Auto | - | FC Sheriff | 0:5 | ||
| 1st(1st leg): 25/09/2019 17:00 | 2nd (2nd leg): 29/10/2019 11:00 | Winner: FC Sheriff | ||||
