David Loewenthal defeated Nicholas Monroe 6-4 7-5 in the Costa Rica F1 round of 32 on hard. The upset overturned the form book — Nicholas Monroe came in leading the head-to-head 1–0. David Loewenthal claimed a first win over Nicholas Monroe in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-05-16 | USA F11 | R32 | clay | Nicholas Monroe | 6-1 3-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.