Gilles Simon defeated Ivo Karlovic 7-6 4-6 7-6 in the Madrid Masters quarter-final on clay. The upset overturned the form book — Ivo Karlovic came in leading the head-to-head 3–0, defending last year's round of 16. Gilles Simon claimed a first win over Ivo Karlovic in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2015-08-16 | Cincinnati Masters | R64 | hard | Ivo Karlovic | 6-4 6-7(3) 6-3 |
| 2011-03-10 | Indian Wells Masters | R32 | hard | Ivo Karlovic | 6-3 6-3 |
| 2007-06-18 | Nottingham | R16 | grass | Ivo Karlovic | 7-6(4) 6-7(4) 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.