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| H | SS Folgore/Falciano | - | SC Faetano | 2:1 | ||
| R | SC Faetano | - | SS Folgore/Falciano | 0:2 | ||
| H: 26.10.2019 15:00 | R: 10.11.2019 15:00 | Sieger: SS Folgore/Falciano | ||||
| H | AC Juvenes/Dogana | - | AC Libertas | 2:1 | ||
| R | AC Libertas | - | AC Juvenes/Dogana | 2:0 | ||
| H: 26.10.2019 15:00 | R: 10.11.2019 15:00 | Sieger: AC Libertas | ||||
| H | SS San Giovanni | - | SS Cosmos | 1:4 | ||
| R | SS Cosmos | - | SS San Giovanni | 1:0 | ||
| H: 26.10.2019 15:00 | R: 10.11.2019 15:00 | Sieger: SS Cosmos | ||||
| H | SS Pennarossa | - | SP La Fiorita | 2:3 | ||
| R | SP La Fiorita | - | SS Pennarossa | 2:2 | ||
| H: 26.10.2019 15:00 | R: 10.11.2019 15:00 | Sieger: SP La Fiorita | ||||
| H | FC Domagnano | - | FC Fiorentino | 2:1 | ||
| R | FC Fiorentino | - | FC Domagnano | 0:0 | ||
| H: 27.10.2019 15:00 | R: 09.11.2019 15:00 | Sieger: FC Domagnano | ||||
| H | SS Virtus | - | SP Cailungo | 1:2 | ||
| R | SP Cailungo | - | SS Virtus | 3:0 | ||
| H: 27.10.2019 15:00 | R: 09.11.2019 15:00 | Sieger: SP Cailungo | ||||
| H | SS Murata | - | SP Tre Penne | 0:2 | ||
| R | SP Tre Penne | - | SS Murata | 2:2 | ||
| H: 27.10.2019 15:00 | R: 09.11.2019 15:00 | Sieger: SP Tre Penne | ||||
