Huntley Montgomery defeated Raven Klaasen 7-5 0-6 6-4 in the USA F6 round of 32 on hard. The upset overturned the form book — Raven Klaasen came in leading the head-to-head 1–0. Huntley Montgomery claimed a first win over Raven Klaasen in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-07-22 | USA F21 | R16 | hard | Raven Klaasen | 6-3 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.