Jan Lennard Struff defeated Stefanos Tsitsipas 6-4 6-7 7-6 in the Cincinnati Masters round of 32 on hard. The upset overturned the form book — Stefanos Tsitsipas came in leading the head-to-head 6–3, defending last year's round of 64. Jan Lennard Struff narrowed the head-to-head to 6–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-04-23 | Madrid Masters | R64 | clay | Stefanos Tsitsipas | 3-6 6-4 6-3 |
| 2024-08-12 | Cincinnati Masters | R64 | hard | Stefanos Tsitsipas | 4-6 6-4 6-3 |
| 2024-06-17 | Halle | R16 | grass | Jan Lennard Struff | 6-4 6-4 |
| 2024-05-06 | Rome Masters | R64 | clay | Stefanos Tsitsipas | 6-7(1) 6-4 6-4 |
| 2023-04-24 | Madrid Masters | QF | clay | Jan Lennard Struff | 7-6(5) 5-7 6-3 |
| 2020-10-26 | Vienna | R32 | hard | Stefanos Tsitsipas | 6-7(3) 6-3 6-4 |
| 2020-02-24 | Dubai | QF | hard | Stefanos Tsitsipas | 4-6 6-4 6-4 |
| 2019-04-22 | Barcelona | R16 | clay | Jan Lennard Struff | 6-4 3-6 6-2 |
| 2019-02-04 | Sofia | R16 | hard | Stefanos Tsitsipas | 7-6(5) 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) · Tsitsipas S.: 12 days rest · 2 matches (14d). Higher means fresher. About