Daniil Medvedev leads the record after 12 meetings.
| Surface | Struff | Medvedev |
|---|---|---|
| Hard | 0 | 7 |
| Clay | 0 | 1 |
| Grass | 2 | 2 |
| Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|
| Shanghai Rolex Masters - Shanghai 2026 | R2 | Hard | Medvedev | 4-6 6-4 6-3 |
| China Open - Beijing 2026 | R2 | Hard | Medvedev | 6-4 6-3 |
| Wimbledon - London 2026 | R3 | Grass | Struff | 7-6(4) 7-6(5) 7-5 |
| Dubai Duty Free Tennis Championships - Dubai 2025 | R1 | Hard | Medvedev | 6-4 7-6(4) |
| Open 13 Provence - Marseille 2025 | QF | Hard (Indoor) | Medvedev | 6-3 6-2 |
| Wimbledon - London 2024 | R3 | Grass | Medvedev | 6-1 6-3 4-6 7-6(3) |
| Davis Cup, Finals, SF, RUS-GER 2-1 2021 | R14 | Hard (Indoor) | Medvedev | 6-4 6-4 |
| Wimbledon - London 2021 | R1 | Grass | Medvedev | 6-4 6-1 4-6 7-6(3) |
| Noventi Open - Halle 2021 | R1 | Grass | Struff | 7-6(6) 6-3 |
| Western & Southern Open - Cincinnati 2019 | R3 | Hard | Medvedev | 6-2 6-1 |
| Open 13 - Marseille 2017 | R2 | Hard (Indoor) | Medvedev | 6-3 3-6 7-6(3) |
| Bet-at-home Open - Hamburg 2016 | R1 | Clay | Medvedev | 6-4 5-7 6-4 |
Meetings are the ones on our record. Older matches may be missing.
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