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| 1st(1st leg) | SS Folgore/Falciano | - | SC Faetano | 2:1 | ||
| 2nd (2nd leg) | SC Faetano | - | SS Folgore/Falciano | 0:2 | ||
| 1st(1st leg): 26/10/2019 14:00 | 2nd (2nd leg): 10/11/2019 14:00 | Winner: SS Folgore/Falciano | ||||
| 1st(1st leg) | AC Juvenes/Dogana | - | AC Libertas | 2:1 | ||
| 2nd (2nd leg) | AC Libertas | - | AC Juvenes/Dogana | 2:0 | ||
| 1st(1st leg): 26/10/2019 14:00 | 2nd (2nd leg): 10/11/2019 14:00 | Winner: AC Libertas | ||||
| 1st(1st leg) | SS San Giovanni | - | SS Cosmos | 1:4 | ||
| 2nd (2nd leg) | SS Cosmos | - | SS San Giovanni | 1:0 | ||
| 1st(1st leg): 26/10/2019 14:00 | 2nd (2nd leg): 10/11/2019 14:00 | Winner: SS Cosmos | ||||
| 1st(1st leg) | SS Pennarossa | - | SP La Fiorita | 2:3 | ||
| 2nd (2nd leg) | SP La Fiorita | - | SS Pennarossa | 2:2 | ||
| 1st(1st leg): 26/10/2019 14:00 | 2nd (2nd leg): 10/11/2019 14:00 | Winner: SP La Fiorita | ||||
| 1st(1st leg) | FC Domagnano | - | FC Fiorentino | 2:1 | ||
| 2nd (2nd leg) | FC Fiorentino | - | FC Domagnano | 0:0 | ||
| 1st(1st leg): 27/10/2019 14:00 | 2nd (2nd leg): 09/11/2019 14:00 | Winner: FC Domagnano | ||||
| 1st(1st leg) | SS Virtus | - | SP Cailungo | 1:2 | ||
| 2nd (2nd leg) | SP Cailungo | - | SS Virtus | 3:0 | ||
| 1st(1st leg): 27/10/2019 14:00 | 2nd (2nd leg): 09/11/2019 14:00 | Winner: SP Cailungo | ||||
| 1st(1st leg) | SS Murata | - | SP Tre Penne | 0:2 | ||
| 2nd (2nd leg) | SP Tre Penne | - | SS Murata | 2:2 | ||
| 1st(1st leg): 27/10/2019 14:00 | 2nd (2nd leg): 09/11/2019 14:00 | Winner: SP Tre Penne | ||||
