Nicholas Monroe advanced when Nima Roshan retired 6-4 4-1 in the USA F13 round of 32. Nicholas Monroe extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-22 | USA F14 | R32 | hard | Nicholas Monroe | 6-4 6-3 |
| 2007-09-17 | USA F23 | R16 | hard | Nima Roshan | 4-6 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.