
Karen Khachanov defeated Philipp Kohlschreiber 3-6 6-3 7-6 in the Moscow round of 16 on hard. The upset overturned the form book — Philipp Kohlschreiber came in leading the head-to-head 3–1. Karen Khachanov narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-04-29 | Munich | R16 | clay | Philipp Kohlschreiber | 7-6(6) 6-4 |
| 2018-05-14 | Rome Masters | R64 | clay | Philipp Kohlschreiber | 7-5 6-7(7) 7-6(6) |
| 2018-02-12 | Rotterdam | R32 | hard | Philipp Kohlschreiber | 3-6 7-6(1) 7-6(5) |
| 2016-07-18 | Kitzbuhel | R16 | clay | Karen Khachanov | 6-4 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.