

Grigor Dimitrov defeated Alexei Popyrin 7-6 6-2 in the Shanghai Masters round of 32 on hard. The upset overturned the form book — Alexei Popyrin came in ranked #128, leading the head-to-head 2–1, defending last year's round of 128. Grigor Dimitrov narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-08-05 | Canada Masters | R16 | hard | Alexei Popyrin | 4-6 7-6 6-3 |
| 2021-08-30 | US Open | R64 | hard | Alexei Popyrin | 7-6 7-6 4-0 |
| 2021-02-01 | Murray River Open | R16 | hard | Grigor Dimitrov | 6-4 6-7 6-3 |
Averages over each player's completed matches in the selected window (114 vs 116). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Dimitrov G.: 9 days rest · 1 match (14d) · Popyrin A.: 3 days rest · 2 matches, 30 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 hard field, opponent-adjusted over 52 weeks). About