Gian Marco Ortenzi defeated S. D'Agostino 5-7 6-3 7-6 in the M15 Gubbio 1 round of 16 on clay. The upset overturned the form book — S. D'Agostino came in ranked #848, leading the head-to-head 1–0. Gian Marco Ortenzi claimed a first win over S. D'Agostino in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-09-12 | M25 Pozzuoli 1 | R32 | hard | S. D'Agostino | 6-4 6-4 |