01/By surface
each with its own count, at equal weight
Hard
1-0
G. leads 1-0 in 1 meeting on hard
Clay
2-0
G. leads 2-0 in 2 meetings on clay
Grass
0-1
J. leads 1-0 in 1 meeting on grass
02/Every meeting
4 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, G. first |
|---|---|---|---|---|---|---|
| May 26, 2019 | French OpenGrand Slam, best of 5 | clay | 1st round | Dimitrov G. | 6-3, 6-0, 3-6, 6-7, 6-4 | 46 v 303 |
| Jan 14, 2019 | Australian OpenGrand Slam, best of 5 | hard | 1st round | Dimitrov G. | 4-6, 6-3, 6-1, 6-4 | 21 v unranked |
| Jun 14, 2016 | AEGON ChampionshipsATP500 | grass | 1st round | Tipsarevic J. | 7-6, 4-6, 6-3 | 37 v 553 |
| Apr 16, 2013 | Monte Carlo MastersMasters 1000 | clay | 2nd round | Dimitrov G. | 7-6, 6-1 | 34 v 10 |
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. Dimitrov G. and Tipsarevic J. each carry the table against every opponent faced.