Tim Smyczek defeated Nicholas Monroe 6-4 6-4 in the USA F6 qualifying round on hard. Tim Smyczek extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-08 | USA F12 | R16 | hard | Tim Smyczek | 2-6 7-5 6-4 |
| 2008-08-09 | Washington | Q32 | hard | Nicholas Monroe | 6-4 3-6 6-4 |
Averages over each player's completed matches in the selected window (200 vs 1). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. Small sample — read as indicative. About