Alexandr Dolgopolov defeated Nicolas Almagro 2-6 7-5 7-6 in the Shanghai Masters round of 64 on hard. The upset overturned the form book — Nicolas Almagro came in leading the head-to-head 4–1, defending last year's round of 32. Alexandr Dolgopolov narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-05-15 | Rome Masters | Q2 | clay | Nicolas Almagro | 7-5 6-4 |
| 2015-05-24 | Roland Garros | R128 | clay | Nicolas Almagro | 6-3 2-6 6-4 7-6(6) |
| 2014-02-17 | Rio de Janeiro | R32 | clay | Alexandr Dolgopolov | 2-6 6-3 6-0 |
| 2011-02-07 | Costa Do Sauipe | F | hard | Nicolas Almagro | 6-3 7-6(3) |
| 2010-05-24 | Roland Garros | R32 | clay | Nicolas Almagro | 6-3 6-3 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.