Gian Marco Ortenzi defeated Antonio Massara 3-6 7-6 10-3 in the M25 Padova 1 q32 on clay. The upset overturned the form book — Antonio Massara came in leading the head-to-head 1–0. Gian Marco Ortenzi claimed a first win over Antonio Massara in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-09-25 | M25 Santa Margherita Di Pula 9 | R32 | clay | Antonio Massara | 6-4 6-1 |