Juan Ignacio Chela defeated Simone Bolelli 7-6 6-7 6-1 in the Umag round of 16 on clay. The upset overturned the form book — Simone Bolelli came in leading the head-to-head 2–0, defending last year's quarter-final. Juan Ignacio Chela claimed a first win over Simone Bolelli in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-10 | Madrid Masters | R64 | clay | Simone Bolelli | 7-5 7-6(3) |
| 2008-04-20 | Monte Carlo Masters | R64 | clay | Simone Bolelli | 6-2 6-2 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (120 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About