Rajeev Ram defeated Huntley Montgomery 4-6 6-3 6-4 in the USA F20 round of 16 on hard. Rajeev Ram extended 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 |
| 2002-10-28 | USA F27 | R32 | hard | Huntley Montgomery | 2-6 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.