01/By surface
each with its own count, at equal weight
Hard
2-0
N. leads 2-0 in 2 meetings on hard
Clay
2-0
N. leads 2-0 in 2 meetings 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, N. first |
|---|---|---|---|---|---|---|
| May 14, 2018 | Internazionali BNL d'ItaliaMasters 1000 | clay | 1st round | Djokovic N. | 6-1, 6-3 | 18 v 54 |
| Aug 22, 2015 | Western & Southern Financial Group MastersMasters 1000 | hard | semifinal | Djokovic N. | 4-6, 7-6, 6-2 | 1 v 66 |
| Mar 31, 2015 | Sony Ericsson OpenMasters 1000 | hard | 4th round | Djokovic N. | 6-7, 7-5, 6-0 | 1 v 65 |
| May 16, 2013 | Internazionali BNL d'ItaliaMasters 1000 | clay | 3rd round | Djokovic N. | 6-1, 6-4 | 1 v 23 |
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. Djokovic N. and Dolgopolov O. each carry the table against every opponent faced.