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| 1st(1st leg) | AC Juvenes/Dogana | - | SS Pennarossa | 0:2 | ||
| 2nd (2nd leg) | SS Pennarossa | - | AC Juvenes/Dogana | 2:1 | ||
| 1st(1st leg): 28/09/2021 19:45 | 2nd (2nd leg): 27/10/2021 19:45 | Winner: SS Pennarossa | ||||
| 1st(1st leg) | SS Cosmos | - | SP Tre Penne | 2:3 | ||
| 2nd (2nd leg) | SP Tre Penne | - | SS Cosmos | 4:2 | ||
| 1st(1st leg): 28/09/2021 19:45 | 2nd (2nd leg): 27/10/2021 19:45 | Winner: SP Tre Penne | ||||
| 1st(1st leg) | SC Faetano | - | SP Cailungo | 0:0 | ||
| 2nd (2nd leg) | SP Cailungo | - | SC Faetano | 0:2 | ||
| 1st(1st leg): 29/09/2021 19:45 | 2nd (2nd leg): 27/10/2021 19:45 | Winner: SC Faetano | ||||
| 1st(1st leg) | FC Fiorentino | - | SP Tre Fiori | 1:1 | ||
| 2nd (2nd leg) | SP Tre Fiori | - | FC Fiorentino | 2:0 | ||
| 1st(1st leg): 29/09/2021 19:45 | 2nd (2nd leg): 26/10/2021 19:45 | Winner: SP Tre Fiori | ||||
| 1st(1st leg) | SS Folgore/Falciano | - | AC Libertas | 1:1 | ||
| 2nd (2nd leg) | AC Libertas | - | SS Folgore/Falciano | 1:5 | ||
| 1st(1st leg): 29/09/2021 19:45 | 2nd (2nd leg): 27/10/2021 19:45 | Winner: SS Folgore/Falciano | ||||
| 1st(1st leg) | SS Virtus | - | SS Murata | 1:2 | ||
| 2nd (2nd leg) | SS Murata | - | SS Virtus | 0:0 | ||
| 1st(1st leg): 29/09/2021 19:45 | 2nd (2nd leg): 27/10/2021 19:45 | Winner: SS Murata | ||||
| 1st(1st leg) | FC Domagnano | - | SS San Giovanni | 2:1 | ||
| 2nd (2nd leg) | SS San Giovanni | - | FC Domagnano | 0:1 | ||
| 1st(1st leg): 29/09/2021 19:45 | 2nd (2nd leg): 26/10/2021 19:45 | Winner: FC Domagnano | ||||
