Juan Monaco defeated Dmitri Sitak 6-7 6-1 6-4 in the Jamaica F21 round of 32 on hard. The result followed the form book — Juan Monaco came in leading the head-to-head 1–0. Juan Monaco extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-05-05 | Jamaica F4 | F | hard | Juan Monaco | 5-7 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.