Janko Tipsarevic defeated Alexandr Dolgopolov 6-4 5-7 6-2 in the Miami Masters round of 32 on hard. The upset overturned the form book — Alexandr Dolgopolov came in leading the head-to-head 2–0, defending last year's round of 16. Janko Tipsarevic claimed a first win over Alexandr Dolgopolov in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-02-13 | Buenos Aires | R32 | clay | Alexandr Dolgopolov | 6-3 6-3 |
| 2013-09-30 | Tokyo | R16 | hard | Alexandr Dolgopolov | 6-3 7-6(2) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.