Nima Roshan defeated Nicholas Monroe 4-6 6-1 6-3 in the USA F23 round of 16 on hard. The upset overturned the form book — Nicholas Monroe came in leading the head-to-head 2–0. Nima Roshan claimed a first win over Nicholas Monroe in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-06-07 | USA F13 | R32 | hard | Nicholas Monroe | 6-4 4-1 |
| 2009-06-22 | USA F14 | R32 | hard | Nicholas Monroe | 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.