| 1. Round | 08/12/2019 | FC Fiorentino | - | SS Pennarossa | 1:4 |  |
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| 5. Round | 02/02/2020 | SS Pennarossa | - | SS Cosmos | 5:1 | ||||
| 6. Round | 08/02/2020 | AC Juvenes/Dogana | - | SS Pennarossa | 0:0 |  |
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| 7. Round | 15/02/2020 | SS San Giovanni | - | SS Pennarossa | 0:3 | ||||
| 8. Round | 23/02/2020 | SS Pennarossa | - | FC Fiorentino | 7:3 |
San Marino