
Jan Lennard Struff defeated Denis Shapovalov 7-6 3-6 6-4 in the Cincinnati Masters round of 32 on hard. The upset overturned the form book — Denis Shapovalov came in ranked #39, defending last year's round of 32. Jan Lennard Struff extended the head-to-head to 7–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-11-20 | Davis Cup Finals QF: GER vs CAN | RR | hard | Jan Lennard Struff | 4-6 7-5 7-6(5) |
| 2022-11-24 | Davis Cup Finals QF: GER vs CAN | RR | hard | Jan Lennard Struff | 6-3 4-6 7-6(2) |
| 2022-01-03 | Atp Cup | RR | hard | Denis Shapovalov | 7-6(5) 4-6 6-3 |
| 2021-10-25 | St. Petersburg | QF | carpet | Jan Lennard Struff | 6-4 6-3 |
| 2021-03-15 | Dubai | R32 | hard | Denis Shapovalov | 6-1 6-3 |
| 2019-06-10 | Stuttgart | R32 | grass | Jan Lennard Struff | 7-5 6-4 |
| 2019-05-27 | Roland Garros | R128 | clay | Jan Lennard Struff | 7-6(1) 6-3 6-4 |
| 2019-04-15 | Monte Carlo Masters | R64 | clay | Jan Lennard Struff | 5-7 6-3 6-1 |
| 2018-10-01 | Tokyo | QF | hard | Denis Shapovalov | 4-6 7-6(7) 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 (200 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Struff J.: 6 days rest · 1 match, 34 games (7d) · Shapovalov D.: 14 days rest · 1 match (14d). Higher means fresher. About