Roberto Bautista Agut defeated Gilles Simon 6-3 7-6 in the Monte Carlo Masters round of 64 on clay. The upset overturned the form book — Gilles Simon came in leading the head-to-head 5–2, defending last year's semi-final. Roberto Bautista Agut narrowed the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2022-01-31 | Montpellier | R16 | hard | Roberto Bautista Agut | 6-4 3-2 RET |
| 2020-10-12 | Cologne 1 | R16 | hard | Roberto Bautista Agut | 6-4 7-6(5) |
| 2018-01-01 | Pune | R16 | hard | Gilles Simon | 6-3 7-6(5) |
| 2016-10-31 | Paris Masters | R32 | hard | Gilles Simon | 2-6 6-1 7-6(6) |
| 2014-09-29 | Tokyo | R32 | hard | Gilles Simon | 4-6 7-6(7) 2-1 RET |
| 2013-02-18 | Marseille | R16 | hard | Gilles Simon | 6-3 6-1 |
| 2012-03-21 | Miami Masters | R64 | hard | Gilles Simon | 6-4 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.