Nahuel Fracassi defeated Stefano Cobolli 7-5 5-7 6-2 in the Italy 3 4 qualifying round on clay. The upset overturned the form book — Stefano Cobolli came in leading the head-to-head 1–0, but Nahuel Fracassi had been the form player, winning 3 of their last 8 on clay. Nahuel Fracassi claimed a first win over Stefano Cobolli in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-21 | Italy 3 Masters 3 | R16 | clay | Stefano Cobolli | 6-1 7-5 |