Sebastien Grosjean defeated Roger Federer 6-4 6-3 in the Monte Carlo Masters quarter-final on clay. The upset overturned the form book — Roger Federer came in leading the head-to-head 3–1, defending last year's round of 64. Sebastien Grosjean narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-08-07 | Canada Masters | R32 | hard | Roger Federer | 6-3 6-3 |
| 2004-06-21 | Wimbledon | SF | grass | Roger Federer | 6-2 6-3 7-6(6) |
| 2001-02-19 | Rotterdam | R16 | hard | Roger Federer | 4-6 6-3 6-4 |
| 2001-01-08 | Sydney | QF | hard | Sebastien Grosjean | 7-5 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