Nicolas Massu defeated Roger Federer 6-7 6-1 6-3 in the Long Island round of 32 on hard. The upset overturned the form book — Roger Federer came in leading the head-to-head 4–0. Nicolas Massu claimed a first win over Roger Federer in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-10-16 | Madrid Masters | R32 | clay | Roger Federer | 6-3 6-2 |
| 2006-05-29 | Roland Garros | R32 | clay | Roger Federer | 6-1 6-2 6-7(4) 7-5 |
| 2006-03-06 | Indian Wells Masters | R64 | hard | Roger Federer | 6-3 7-6(4) |
| 2001-10-08 | Vienna | R32 | hard | Roger Federer | 4-6 7-6(8) 6-4 |
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 (200 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About