

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 #142, defending last year's round of 16. 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 4-6 7-6 |
| 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 6-3 6-3 |
| 2014-08-25 | US Open | R16 | hard | Gael Monfils | 7-5 7-6 7-5 |
| 2014-04-21 | Bucharest | SF | clay | Grigor Dimitrov | 5-1 |
| 2011-08-29 | US Open | R128 | hard | Gael Monfils | 7-6 6-3 6-4 |
Averages over each player's completed matches in the selected window (199 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, 18 games (7d). Higher means fresher. About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About