

Marin Cilic defeated Denis Shapovalov 7-5 7-6 in the Stuttgart quarter-final on grass. The upset overturned the form book — Denis Shapovalov came in ranked #48. Marin Cilic extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2026-06-08 | s Hertogenbosch | R32 | grass | Marin Cilic | 6-4 7-5 |
| 2026-01-19 | Australian Open | R64 | hard | Marin Cilic | 6-4 6-3 6-2 |
| 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 (199 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Cilic M.: 6 days rest · 1 match, 23 games (7d) · Shapovalov D.: 5 days rest · 2 matches, 51 games (7d). Higher means fresher. About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About