Heather Watson defeated Anett Kontaveit 6-1 6-1 in the Roland Garros qualifying final on clay. The upset overturned the form book — Anett Kontaveit came in leading the head-to-head 4–1. Heather Watson narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-02-08 | Australian Open | R64 | hard | Anett Kontaveit | 6-7(5) 6-4 6-2 |
| 2019-07-01 | Wimbledon | R64 | grass | Anett Kontaveit | 7-5 6-1 |
| 2018-01-01 | Brisbane | R32 | hard | Anett Kontaveit | 6-0 6-3 |
| 2017-10-16 | Luxembourg | R16 | hard | Heather Watson | 6-4 6-4 |
| 2017-04-10 | Biel | R32 | hard | Anett Kontaveit | 7-6(2) 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.