01/By surface
each with its own count, at equal weight
Hard
2-1
S. leads 2-1 in 3 meetings on hard
Clay
1-0
S. leads 1-0 in 1 meeting on clay
Grass
Never on grass
no meeting on this surface
02/Every meeting
4 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, S. first |
|---|---|---|---|---|---|---|
| Aug 24, 2020 | Western & Southern Financial Group MastersMasters 1000 | hard | 2nd round | Tsitsipas S. | 6-1, 6-3 | 6 v 124 |
| Oct 11, 2018 | Shanghai MastersMasters 1000 | hard | 3rd round | Anderson K. | 6-4, 7-6 | 15 v 8 |
| Aug 11, 2018 | Rogers MastersMasters 1000 | hard | semifinal | Tsitsipas S. | 6-7, 6-4, 7-6 | 27 v 6 |
| May 3, 2018 | Millennium Estoril OpenATP250 | clay | 2nd round | Tsitsipas S. | 6-7, 6-3, 6-3 | 44 v 8 |
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. Tsitsipas S. and Anderson K. each carry the table against every opponent faced.