Anett Kontaveit defeated Kirsten Flipkens 3-6 6-1 6-2 in the 's Hertogenbosch round of 16 on grass. The upset overturned the form book — Kirsten Flipkens came in leading the head-to-head 1–0, defending last year's round of 32. Anett Kontaveit claimed a first win over Kirsten Flipkens in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-02-29 | Monterrey | SF | hard | Kirsten Flipkens | 7-6(6) 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.