Yohny Romero defeated Phillip King 3-6 6-1 6-4 in the USA F16 round of 64 on hard. The upset overturned the form book — Phillip King came in leading the head-to-head 1–0, but Yohny Romero had been the form player, winning 5 of their last 9 on hard. Yohny Romero claimed a first win over Phillip King in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | USA F7 | R16 | hard | Phillip King | 6-1 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.