

Grigor Dimitrov advanced when Gael Monfils retired 5-1 in the Bucharest semi-final. Grigor Dimitrov narrowed 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 |
| 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 |
| 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
Averages over each player's completed matches in the selected window (200 vs 199). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Dimitrov G.: 8 days rest · 4 matches (14d). Higher means fresher. About