Denis Shapovalov defeated Daniil Medvedev 7-5 6-1 6-2 in the US Open round of 128 on hard. The upset overturned the form book — Daniil Medvedev came in ranked #8, leading the head-to-head 4–1. Denis Shapovalov narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2022-10-24 | Vienna | F | hard | Daniil Medvedev | 4-6 6-3 6-2 |
| 2022-08-15 | Cincinnati Masters | R16 | hard | Daniil Medvedev | 7-5 7-5 |
| 2021-09-24 | Laver Cup | RR | hard | Daniil Medvedev | 6-4 6-0 |
| 2018-10-01 | Tokyo | SF | hard | Daniil Medvedev | 6-3 6-3 |
| 2018-07-30 | Washington | R32 | hard | Denis Shapovalov | 3-6 6-1 6-4 |
Averages from each player's recent completed matches (20 vs 19). ATP, WTA & Challenger.