01/By surface
each with its own count, at equal weight
Hard
1-4
S. leads 4-1 in 5 meetings on hard
Clay
2-2
Level 2-2 in 4 meetings on clay
Grass
1-0
J.L. leads 1-0 in 1 meeting on grass
02/Every meeting
10 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, J.L. first |
|---|---|---|---|---|---|---|
| Apr 26, 2025 | Mutua Madrid OpenMasters 1000 | clay | 2nd round | Tsitsipas S. | 3-6, 6-4, 6-3 | 79 v 18 |
| Aug 14, 2024 | Western & Southern Financial Group MastersMasters 1000 | hard | 1st round | Tsitsipas S. | 4-6, 6-4, 6-3 | 36 v 11 |
| Jun 20, 2024 | Halle OpenATP500 | grass | 2nd round | Struff J.L. | 6-4, 6-4 | 41 v 11 |
| May 11, 2024 | Internazionali BNL d'ItaliaMasters 1000 | clay | 2nd round | Tsitsipas S. | 6-7, 6-4, 6-4 | 41 v 8 |
| May 4, 2023 | Mutua Madrid OpenMasters 1000 | clay | quarterfinal | Struff J.L. | 7-6, 5-7, 6-3 | 65 v 5 |
| Oct 28, 2020 | Erste Bank OpenATP500 | hard | 1st round | Tsitsipas S. | 6-7, 6-3, 6-4 | 34 v 5 |
| Feb 27, 2020 | Dubai Tennis ChampionshipsATP500 | hard | quarterfinal | Tsitsipas S. | 4-6, 6-4, 6-4 | 34 v 6 |
| Aug 14, 2019 | Western & Southern Financial Group MastersMasters 1000 | hard | 2nd round | Struff J.L. | 6-4, 6-7, 7-6 | 36 v 7 |
| Apr 25, 2019 | Open Banco SabadellATP500 | clay | 3rd round | Struff J.L. | 6-4, 3-6, 6-2 | 51 v 8 |
| Feb 7, 2019 | Sofia OpenATP250 | hard | 2nd round | Tsitsipas S. | 7-6, 6-4 | 51 v 12 |
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 Tsitsipas S. each carry the table against every opponent faced.