01/By surface
each with its own count, at equal weight
Hard
0-4
D. leads 4-0 in 4 meetings on hard
Clay
0-1
D. leads 1-0 in 1 meeting on clay
Grass
2-2
Level 2-2 in 4 meetings on grass
02/Every meeting
9 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, J.L. first |
|---|---|---|---|---|---|---|
| Jul 3, 2026 | WimbledonGrand Slam, best of 5 | grass | 3rd round | Struff J.L. | 7-6, 7-6, 7-5 | 74 v 9 |
| Feb 25, 2025 | Dubai Tennis ChampionshipsATP500 | hard | 1st round | Medvedev D. | 6-4, 7-6 | 46 v 6 |
| Feb 14, 2025 | Open 13ATP250 | hard | quarterfinal | Medvedev D. | 6-3, 6-2 | 46 v 8 |
| Jul 6, 2024 | WimbledonGrand Slam, best of 5 | grass | 3rd round | Medvedev D. | 6-1, 6-3, 4-6, 7-6 | 41 v 5 |
| Jun 29, 2021 | WimbledonGrand Slam, best of 5 | grass | 1st round | Medvedev D. | 6-4, 6-1, 4-6, 7-6 | 45 v 2 |
| Jun 15, 2021 | Halle OpenATP500 | grass | 1st round | Struff J.L. | 7-6, 6-3 | 45 v 2 |
| Aug 15, 2019 | Western & Southern Financial Group MastersMasters 1000 | hard | 3rd round | Medvedev D. | 6-2, 6-1 | 36 v 8 |
| Feb 23, 2017 | Open 13ATP250 | hard | 2nd round | Medvedev D. | 6-3, 3-6, 7-6 | 62 v 64 |
| Jul 12, 2016 | German Tennis ChampionshipsATP500 | clay | 1st round | Medvedev D. | 6-4, 5-7, 6-4 | 86 v 215 |
A record, never a share of meetings. Main-draw singles since 2013; a meeting ended by retirement is counted with the sets that were played and marked; a walkover is listed and counted in neither column. Struff J.L. and Medvedev D. each carry the table against every opponent faced.