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| 1st(1st leg) | SC Faetano | - | SP Tre Fiori | 2:2 (0:2) | ||
| 2nd (2nd leg) | SP Tre Fiori | - | SC Faetano | 4:2 (0:0, 0:0, 0:0) pso | ||
| 1st(1st leg): 27/09/2023 20:15 | 2nd (2nd leg): 26/10/2023 19:45 | Winner: SP Tre Fiori | ||||
| 1st(1st leg) | SP La Fiorita | - | SP Cailungo | 1:0 (1:0) | ||
| 2nd (2nd leg) | SP Cailungo | - | SP La Fiorita | 0:1 (0:0) | ||
| 1st(1st leg): 27/09/2023 20:15 | 2nd (2nd leg): 25/10/2023 19:45 | Winner: SP La Fiorita | ||||
| 1st(1st leg) | FC Fiorentino | - | SS San Giovanni | 4:1 (4:1) | ||
| 2nd (2nd leg) | SS San Giovanni | - | FC Fiorentino | 1:2 (1:1) | ||
| 1st(1st leg): 27/09/2023 20:15 | 2nd (2nd leg): 25/10/2023 19:45 | Winner: FC Fiorentino | ||||
| 1st(1st leg) | AC Juvenes/Dogana | - | AC Libertas | 1:1 (0:1) | ||
| 2nd (2nd leg) | AC Libertas | - | AC Juvenes/Dogana | 5:0 (2:0) | ||
| 1st(1st leg): 27/09/2023 20:15 | 2nd (2nd leg): 25/10/2023 19:45 | Winner: AC Libertas | ||||
| 1st(1st leg) | SS Cosmos | - | SP Tre Penne | 1:1 (1:0) | ||
| 2nd (2nd leg) | SP Tre Penne | - | SS Cosmos | 2:1 (1:0, 1:1) aet | ||
| 1st(1st leg): 27/09/2023 20:15 | 2nd (2nd leg): 26/10/2023 19:45 | Winner: SP Tre Penne | ||||
| 1st(1st leg) | SS Murata | - | FC Domagnano | 0:0 (0:0) | ||
| 2nd (2nd leg) | FC Domagnano | - | SS Murata | 2:0 (1:0) | ||
| 1st(1st leg): 28/09/2023 20:15 | 2nd (2nd leg): 25/10/2023 19:45 | Winner: FC Domagnano | ||||
| 1st(1st leg) | SS Folgore/Falciano | - | SS Pennarossa | 1:0 (1:0) | ||
| 2nd (2nd leg) | SS Pennarossa | - | SS Folgore/Falciano | 2:4 (1:3) | ||
| 1st(1st leg): 28/09/2023 20:15 | 2nd (2nd leg): 25/10/2023 19:45 | Winner: SS Folgore/Falciano | ||||
