

Gael Monfils defeated Grigor Dimitrov 6-7 6-3 6-3 in the Miami Masters round of 16 on hard. The upset overturned the form book — Grigor Dimitrov came in ranked #146, defending last year's round of 32. 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 |
| 2015-04-12 | Monte Carlo Masters | QF | clay | Gael Monfils | 6-1 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 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Per-surface Serve / Return Rating (0–100, percentile within the hard field, opponent-adjusted over 52 weeks). About
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, 54 games (7d). Higher means fresher. About