Benoit Paire defeated Gilles Simon 7-5 7-6 in the Montpellier quarter-final on hard. The upset overturned the form book — Gilles Simon came in leading the head-to-head 6–3, defending last year's semi-final. Benoit Paire narrowed the head-to-head to 6–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-08-23 | Winston-Salem | R32 | hard | Benoit Paire | 6-3 6-3 |
| 2018-12-31 | Pune | QF | hard | Gilles Simon | 3-6 7-6(4) 6-4 |
| 2018-04-09 | Marrakech | R32 | clay | Gilles Simon | 6-2 6-7(1) 7-6(5) |
| 2015-11-02 | Paris Masters | R32 | hard | Gilles Simon | 6-4 4-6 6-1 |
| 2015-04-12 | Monte Carlo Masters | R32 | clay | Gilles Simon | 6-4 7-5 |
| 2014-05-04 | Madrid Masters | R64 | clay | Gilles Simon | 2-0 RET |
| 2013-10-07 | Shanghai Masters | R64 | hard | Benoit Paire | 6-4 6-3 |
| 2013-03-07 | Indian Wells Masters | R32 | hard | Gilles Simon | 3-6 7-6(5) 6-4 |
| 2011-02-07 | Rotterdam | R32 | hard | Benoit Paire | 6-2 2-6 6-3 |
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.