
Grigor Dimitrov defeated Jannik Sinner 4-6 6-4 6-4 in the Rome Masters round of 16 on clay. The upset overturned the form book — Jannik Sinner came in ranked #1, leading the head-to-head 5–0, defending last year's round of 32. Grigor Dimitrov claimed a first win over Jannik Sinner in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-06-30 | Wimbledon | R16 | grass | Jannik Sinner | 3-6 5-7 2-2 |
| 2024-05-27 | Roland Garros | QF | clay | Jannik Sinner | 6-2 6-4 7-6 |
| 2024-03-18 | Miami Masters | F | hard | Jannik Sinner | 6-3 6-1 |
| 2023-09-27 | Beijing | QF | hard | Jannik Sinner | 6-4 3-6 6-2 |
| 2023-03-20 | Miami Masters | R32 | hard | Jannik Sinner | 6-3 6-4 |
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.: 4 days rest · 1 match, 26 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
Per-surface Serve / Return Rating (0–100, percentile within the clay field, opponent-adjusted over 52 weeks). About