| 1. Round | 21/09/2019 | SS Pennarossa | - | AC Juvenes/Dogana | 3:2 | ||||
| 2. Round | 27/09/2019 | AC Juvenes/Dogana | - | SC Faetano | 0:2 | ||||
| 3. Round | 06/10/2019 | AC Juvenes/Dogana | - | SS Murata | 0:3 | ||||
| 4. Round | 20/10/2019 | FC Domagnano | - | AC Juvenes/Dogana | 2:1 | ||||
| 5. Round | 02/11/2019 | AC Juvenes/Dogana | - | SS Folgore/Falciano | 1:5 | ||||
| 6. Round | 23/11/2019 | AC Juvenes/Dogana | - | SP La Fiorita | 1:3 | ||||
| 7. Round | 01/12/2019 | SP Tre Fiori | - | AC Juvenes/Dogana | 4:0 |  |
San Marino