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| 1st(1st leg) | SP La Fiorita | - | AC Juvenes/Dogana | 1:0 | ||
| 2nd (2nd leg) | AC Juvenes/Dogana | - | SP La Fiorita | 0:5 | ||
| 1st(1st leg): 25/04/2019 19:45 | 2nd (2nd leg): 02/05/2019 19:45 | Winner: SP La Fiorita | ||||
| 1st(1st leg) | AC Libertas | - | SS Murata | 1:0 | ||
| 2nd (2nd leg) | SS Murata | - | AC Libertas | 0:4 | ||
| 1st(1st leg): 26/04/2019 19:45 | 2nd (2nd leg): 03/05/2019 19:45 | Winner: AC Libertas | ||||
| 1st(1st leg) | SP Tre Fiori | - | FC Fiorentino | 2:1 | ||
| 2nd (2nd leg) | FC Fiorentino | - | SP Tre Fiori | 0:1 | ||
| 1st(1st leg): 27/04/2019 14:00 | 2nd (2nd leg): 04/05/2019 14:00 | Winner: SP Tre Fiori | ||||
| 1st(1st leg) | SP Tre Penne | - | SS Folgore/Falciano | 1:0 | ||
| 2nd (2nd leg) | SS Folgore/Falciano | - | SP Tre Penne | 1:1 | ||
| 1st(1st leg): 28/04/2019 14:00 | 2nd (2nd leg): 05/05/2019 14:00 | Winner: SP Tre Penne | ||||
