Anett Kontaveit defeated Venus Williams 3-6 6-3 6-2 in the Madrid round of 64 on clay. The upset overturned the form book — Venus Williams came in leading the head-to-head 2–1. Anett Kontaveit narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2018-05-14 | Rome | R16 | clay | Anett Kontaveit | 6-2 7-6(3) |
| 2016-05-23 | Roland Garros | R128 | clay | Venus Williams | 7-6(5) 7-6(4) |
| 2015-08-31 | US Open | R16 | hard | Venus Williams | 6-2 6-1 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (198 vs 108). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About