Gilles Simon defeated Grigor Dimitrov 6-4 6-3 in the Monte Carlo Masters round of 32 on clay. Gilles Simon extended the head-to-head to 5–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2018-04-23 | Barcelona | R32 | clay | Grigor Dimitrov | 6-2 6-1 |
| 2016-08-15 | Cincinnati Masters | R64 | hard | Grigor Dimitrov | 6-1 6-3 |
| 2016-06-27 | Wimbledon | R64 | grass | Grigor Dimitrov | 6-3 7-6(1) 4-6 6-4 |
| 2016-01-04 | Brisbane | R32 | hard | Grigor Dimitrov | 6-3 7-6(10) |
| 2012-07-25 | London Olympics | R32 | grass | Gilles Simon | 6-3 6-3 |
| 2012-05-20 | Nice | R16 | clay | Gilles Simon | 6-3 6-3 |
| 2009-06-08 | Queen's Club | R32 | grass | Gilles Simon | 7-6(7) 7-6(5) |
| 2009-02-16 | Marseille | R32 | hard | Gilles Simon | 4-6 6-3 7-5 |
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.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Dimitrov G.: 7 days rest · 1 match, 54 games (7d). Higher means fresher. About