Nicolas Todero defeated Nicholas Monroe 4-6 6-2 6-2 in the USA F4 qualifying round on hard. The result followed the form book — Nicolas Todero came in leading the head-to-head 1–0. Nicolas Todero extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-01-19 | USA F2 | QF | clay | Nicolas Todero | 6-7(4) 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.