
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 RET |
| 2024-05-27 | Roland Garros | QF | clay | Jannik Sinner | 6-2 6-4 7-6(3) |
| 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 from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.