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| 1st(1st leg) | SS Virtus | - | FC Domagnano | 2:1 (0:0) | ||
| 2nd (2nd leg) | FC Domagnano | - | SS Virtus | 0:2 (0:1) | ||
| 1st(1st leg): 08/11/2023 19:45 | 2nd (2nd leg): 06/12/2023 19:45 | Winner: SS Virtus | ||||
| 1st(1st leg) | SS Folgore/Falciano | - | SP Tre Fiori | 0:1 (0:1) | ||
| 2nd (2nd leg) | SP Tre Fiori | - | SS Folgore/Falciano | 0:0 (0:0) | ||
| 1st(1st leg): 08/11/2023 19:45 | 2nd (2nd leg): 06/12/2023 19:45 | Winner: SP Tre Fiori | ||||
| 1st(1st leg) | SP La Fiorita | - | FC Fiorentino | 2:1 (0:0) | ||
| 2nd (2nd leg) | FC Fiorentino | - | SP La Fiorita | 1:4 (0:2) | ||
| 1st(1st leg): 08/11/2023 19:45 | 2nd (2nd leg): 06/12/2023 19:45 | Winner: SP La Fiorita | ||||
| 1st(1st leg) | AC Libertas | - | SP Tre Penne | 1:3 (0:3) | ||
| 2nd (2nd leg) | SP Tre Penne | - | AC Libertas | 5:1 (3:1) | ||
| 1st(1st leg): 08/11/2023 19:45 | 2nd (2nd leg): 06/12/2023 19:45 | Winner: SP Tre Penne | ||||
