Simone Bolelli defeated Stan Wawrinka 7-6 6-3 7-6 in the Wimbledon round of 64 on grass. The upset overturned the form book — Stan Wawrinka came in leading the head-to-head 2–0, defending last year's round of 128. Simone Bolelli claimed a first win over Stan Wawrinka in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-08-25 | US Open | R128 | hard | Stan Wawrinka | 7-6 6-3 6-3 |
| 2008-07-21 | Canada Masters | R64 | hard | Stan Wawrinka | 6-4 7-6 |
Averages over each player's completed matches in the selected window (200 vs 198). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Wawrinka S.: 1 day rest · 2 matches, 45 games (7d). Higher means fresher. About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About