Gilles Simon defeated Ivan Ljubicic 7-5 7-6 in the Madrid Masters round of 64 on clay. The upset overturned the form book — Ivan Ljubicic came in leading the head-to-head 3–1. Gilles Simon narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-11-08 | Paris Masters | R32 | hard | Gilles Simon | 6-3 3-6 7-6(4) |
| 2009-05-10 | Madrid Masters | R16 | clay | Ivan Ljubicic | 3-6 6-4 6-3 |
| 2009-03-12 | Indian Wells Masters | R32 | hard | Ivan Ljubicic | 6-3 7-6(3) |
| 2006-04-17 | Monte Carlo Masters | R16 | clay | Ivan Ljubicic | 6-3 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 (200 vs 52). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About