

Gael Monfils defeated Grigor Dimitrov 6-1 6-3 in the Monte Carlo Masters quarter-final on clay. The upset overturned the form book — Grigor Dimitrov came in ranked #168, defending last year's round of 16, but Gael Monfils had been the form player, winning 1 of their last 4 on clay. Gael Monfils extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-03-05 | Indian Wells Masters | R32 | hard | Grigor Dimitrov | 7-6(4) 4-6 7-6(2) |
| 2024-07-01 | Wimbledon | R32 | grass | Grigor Dimitrov | 6-3 6-4 6-3 |
| 2016-03-21 | Miami Masters | R16 | hard | Gael Monfils | 6-7(5) 6-3 6-3 |
| 2014-08-25 | US Open | R16 | hard | Gael Monfils | 7-5 7-6(6) 7-5 |
| 2014-04-21 | Bucharest | SF | clay | Grigor Dimitrov | 5-1 RET |
| 2011-08-29 | US Open | R128 | hard | Gael Monfils | 7-6(4) 6-3 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.