Nicholas Monroe defeated Chris Klingemann 6-2 6-4 in the Canada F5 semi-final on hard. The result followed the form book — Nicholas Monroe came in leading the head-to-head 2–0. Nicholas Monroe extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-09-20 | Canada F4 | R16 | hard | Nicholas Monroe | 7-5 6-0 |
| 2009-01-26 | Mexico F1 | F | hard | Nicholas Monroe | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.