Huntley Montgomery defeated Rajeev Ram 2-6 6-3 6-1 in the USA F27 round of 32 on hard. The upset overturned the form book — Rajeev Ram came in leading the head-to-head 2–0, but Huntley Montgomery had been the form player, winning 3 of their last 4 on hard. Huntley Montgomery claimed a first win over Rajeev Ram in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-03-22 | USA F8 | R16 | hard | Rajeev Ram | 6-1 6-3 |
| 2002-07-15 | USA F20 | R16 | hard | Rajeev Ram | 4-6 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.