Kobi Ziv defeated Ralph Grambow 3-6 6-2 6-2 in the USA F20 round of 64 on hard. The upset overturned the form book — Ralph Grambow came in leading the head-to-head 1–0. Kobi Ziv claimed a first win over Ralph Grambow in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | USA F19 | QF | hard | Ralph Grambow | 6-2 6-2 |