Venus Williams defeated Simona Halep 6-1 4-6 7-6 in the Madrid round of 64 on clay. The upset overturned the form book — Simona Halep came in leading the head-to-head 4–2, defending last year's round of 64. Venus Williams narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-03-18 | Miami | R16 | hard | Simona Halep | 6-3 6-3 |
| 2019-01-14 | Australian Open | R32 | hard | Simona Halep | 6-2 6-3 |
| 2018-08-06 | Montreal | R16 | hard | Simona Halep | 6-2 6-2 |
| 2015-05-11 | Rome | R16 | clay | Simona Halep | 6-2 6-1 |
| 2013-09-23 | Tokyo | R16 | hard | Venus Williams | 4-6 7-5 6-3 |
| 2012-05-14 | Rome | R64 | clay | Venus Williams | 6-3 6-4 |
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 (199 vs 197). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About