Mikhail Kukushkin defeated Damir Dzumhur 7-6 6-2 in the St. Petersburg round of 16 on carpet. The upset overturned the form book — Damir Dzumhur came in ranked #103, leading the head-to-head 3–1, defending last year's quarter-final. Mikhail Kukushkin narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-07-29 | Los Cabos | R32 | hard | Mikhail Kukushkin | 7-5 6-2 |
| 2019-02-11 | Rotterdam | R16 | hard | Damir Dzumhur | 6-4 7-6(3) |
| 2018-02-19 | Marseille | R32 | hard | Damir Dzumhur | 6-7(6) 7-6(3) 6-1 |
| 2016-03-21 | Miami Masters | R32 | hard | Damir Dzumhur | 4-6 6-1 6-2 |
Averages from each player's recent completed matches (19 vs 20). ATP, WTA & Challenger.