Denis Shapovalov defeated Milos Raonic 6-4 6-4 in the Madrid Masters round of 16 on clay. The upset overturned the form book — Milos Raonic came in leading the head-to-head 1–0, defending last year's round of 16. Denis Shapovalov claimed a first win over Milos Raonic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2018-08-13 | Cincinnati Masters | R16 | hard | Milos Raonic | 7-6(6) 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.