Gilles Simon defeated Rafael Nadal 3-6 7-5 7-6 in the Madrid Masters semi-final on clay. The upset overturned the form book — Rafael Nadal came in leading the head-to-head 8–0, defending last year's quarter-final. Gilles Simon claimed a first win over Rafael Nadal in nine meetings, narrowing the head-to-head to 8–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-08-08 | Rio Olympics | R16 | hard | Rafael Nadal | 7-6(5) 6-3 |
| 2015-03-12 | Indian Wells Masters | R16 | hard | Rafael Nadal | 6-2 6-4 |
| 2014-05-11 | Rome Masters | R32 | clay | Rafael Nadal | 7-6(1) 6-7(4) 6-2 |
| 2012-04-15 | Monte Carlo Masters | SF | clay | Rafael Nadal | 6-3 6-4 |
| 2010-08-30 | US Open | R32 | hard | Rafael Nadal | 6-4 6-4 6-2 |
| 2009-01-19 | Australian Open | QF | hard | Rafael Nadal | 6-2 7-5 7-5 |
| 2008-01-14 | Australian Open | R32 | hard | Rafael Nadal | 7-5 6-2 6-3 |
| 2006-02-13 | Marseille | R16 | hard | Rafael Nadal | 7-5 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.