Coco Vandeweghe defeated Alison Riske Amritraj 7-6 3-6 7-6 in the S-Hertogenbosch quarter-final on grass. The upset overturned the form book — Alison Riske Amritraj came in leading the head-to-head 3–2. Coco Vandeweghe narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-08-02 | San Jose | R32 | hard | Alison Riske Amritraj | 6-3 6-4 |
| 2017-08-28 | US Open | R128 | hard | Coco Vandeweghe | 2-6 6-3 6-4 |
| 2017-07-03 | Wimbledon | R32 | grass | Coco Vandeweghe | 6-2 6-4 |
| 2017-02-20 | Dubai | R64 | hard | Alison Riske Amritraj | 6-4 6-4 |
| 2016-07-18 | Stanford | QF | hard | Alison Riske Amritraj | 6-3 0-1 RET |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.