Mikhail Youzhny defeated Milos Raonic 2-6 7-6 6-4 in the St. Petersburg round of 16 on carpet. The upset overturned the form book — Milos Raonic came in leading the head-to-head 3–0, defending the title. Mikhail Youzhny claimed a first win over Milos Raonic in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-07-03 | Wimbledon | R64 | grass | Milos Raonic | 3-6 7-6(7) 6-4 7-5 |
| 2013-08-05 | Canada Masters | R32 | hard | Milos Raonic | 6-4 6-4 |
| 2011-01-17 | Australian Open | R32 | hard | Milos Raonic | 6-4 7-5 4-6 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.