Daniil Medvedev defeated Milos Raonic 7-6 6-3 in the Tokyo quarter-final on hard. The result followed the form book — Daniil Medvedev came in leading the head-to-head 2–0, defending last year's round of 32. Daniil Medvedev extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-11-02 | Paris Masters | SF | hard | Daniil Medvedev | 6-4 7-6(4) |
| 2018-12-31 | Brisbane | QF | hard | Daniil Medvedev | 6-7(2) 6-3 6-4 |
Averages from each player's recent completed matches (19 vs 20). ATP, WTA & Challenger.