Ruxandra Dragomir Ilie defeated Kristie Boogert 7-5 6-2 in the US Open round of 128 on hard. The upset overturned the form book — Kristie Boogert came in leading the head-to-head 1–0, defending last year's round of 64. Ruxandra Dragomir Ilie claimed a first win over Kristie Boogert in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | s Hertogenbosch | R32 | grass | Kristie Boogert | 6-3 4-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.