Paul Henri Mathieu defeated Gilles Simon 6-4 6-3 in the New Haven quarter-final on hard. Paul Henri Mathieu extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-04-25 | Estoril | R16 | clay | Gilles Simon | 3-6 6-2 6-1 |
| 2012-06-25 | Wimbledon | R128 | grass | Gilles Simon | 6-3 5-4 RET |
| 2008-02-11 | Marseille | QF | hard | Paul Henri Mathieu | 6-3 6-4 |
| 2007-05-28 | Roland Garros | R64 | clay | Paul Henri Mathieu | 3-6 6-4 6-1 7-6(2) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.