Justin Bower defeated Michael Jessup 6-1 6-3 in the USA F4 qualifying round on hard. The result followed the form book — Justin Bower came in leading the head-to-head 1–0. Justin Bower extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-11-20 | USA F28 | R32 | hard | Justin Bower | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.