Justin Bower defeated Jose De Armas 6-0 5-7 6-4 in the USA F7 round of 16 on hard. The upset overturned the form book — Jose De Armas came in leading the head-to-head 1–0, but Justin Bower had been the form player, winning 7 of their last 8 on hard. Justin Bower claimed a first win over Jose De Armas in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-15 | USA F12 | SF | clay | Jose De Armas | 7-6(5) 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.