

Marin Cilic defeated Denis Shapovalov 6-4 7-5 in the s Hertogenbosch round of 32 on grass. The upset overturned the form book — Denis Shapovalov came in ranked #67. Marin Cilic extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2026-01-19 | Australian Open | R64 | hard | Marin Cilic | 6-4 6-3 6-2 |
| 2021-06-07 | Stuttgart | QF | grass | Marin Cilic | 7-5 7-6 |
| 2020-08-24 | Cincinnati Masters | R64 | hard | Denis Shapovalov | 6-3 6-3 |
| 2020-02-17 | Marseille | R16 | hard | Denis Shapovalov | 6-4 4-6 6-2 |
| 2019-03-04 | Indian Wells Masters | R32 | hard | Denis Shapovalov | 6-4 6-2 |
| 2018-10-22 | Basel | R32 | hard | Marin Cilic | 6-4 6-2 |
Averages over each player's completed matches in the selected window (18 vs 17). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About