Stefano Cobolli defeated Markus Polessnig 6-3 6-2 in the Italy 3 4 round of 16 on clay. The upset overturned the form book — Markus Polessnig came in leading the head-to-head 1–0. Stefano Cobolli claimed a first win over Markus Polessnig in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-19 | Italy 3 1 | SF | clay | Markus Polessnig | 7-5 2-6 7-6(6) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.