Jose De Armas defeated David Sherwood 7-5 4-6 7-6 in the USA F28 round of 16 on hard. The result followed the form book — Jose De Armas came in leading the head-to-head 1–0. Jose De Armas extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-11-18 | USA F29 | R32 | hard | Jose De Armas | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.