Ralph Grambow defeated Kobi Ziv 6-2 6-2 in the USA F19 qualifying round on hard. The upset overturned the form book — Kobi Ziv came in leading the head-to-head 1–0, but Ralph Grambow had been the form player, winning 3 of their last 8 on hard. Ralph Grambow claimed a first win over Kobi Ziv in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-22 | USA F20 | R64 | hard | Kobi Ziv | 3-6 6-2 6-2 |