
Jan Lennard Struff defeated Marin Cilic 6-2 6-3 in the Rome Masters round of 32 on clay. The upset overturned the form book — Marin Cilic came in ranked #46, defending last year's semi-final. Jan Lennard Struff extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-01-01 | Hong Kong | R32 | hard | Jan Lennard Struff | 3-6 7-6(4) 7-6(7) |
| 2019-05-06 | Madrid Masters | R32 | clay | Marin Cilic | 4-6 6-3 6-4 |
| 2018-10-01 | Tokyo | R32 | hard | Jan Lennard Struff | 3-6 6-4 7-6(1) |
| 2014-01-06 | Sydney | R32 | hard | Marin Cilic | 3-6 6-3 6-3 |
Averages from each player's recent completed matches (20 vs 19). ATP, WTA & Challenger.