01/By surface
each with its own count, at equal weight
Hard
2-3
D. leads 3-2 in 5 meetings on hard
Clay
Never on clay
no meeting on this surface
Grass
2-0
M. leads 2-0 in 2 meetings on grass
02/Every meeting
7 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, M. first |
|---|---|---|---|---|---|---|
| Jun 8, 2026 | Rosmalen Grass Court ChampionshipsATP250 | grass | 1st round | Cilic M. | 6-7, 6-4, 7-5 | 47 v 42 |
| Jan 22, 2026 | Australian OpenGrand Slam, best of 5 | hard | 2nd round | Cilic M. | 6-4, 6-3, 6-2 | 70 v 23 |
| Jun 11, 2021 | Mercedes CupATP250 | grass | quarterfinal | Cilic M. | 7-5, 7-6 | 47 v 14 |
| Aug 23, 2020 | Western & Southern Financial Group MastersMasters 1000 | hard | 1st round | Shapovalov D. | 6-3, 6-3 | 37 v 17 |
| Feb 20, 2020 | Open 13ATP250 | hard | 2nd round | Shapovalov D. | 6-4, 4-6, 6-2 | 39 v 15 |
| Mar 12, 2019 | BNP Paribas OpenMasters 1000 | hard | 3rd round | Shapovalov D. | 6-4, 6-2 | 11 v 25 |
| Oct 22, 2018 | Swiss IndoorsATP500 | hard | 1st round | Cilic M. | 6-4, 6-2 | 6 v 29 |
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. Cilic M. and Shapovalov D. each carry the table against every opponent faced.