Ryan Sachire defeated Michael Jessup 7-5 3-6 6-3 in the USA F16 round of 32 on hard. The result followed the form book — Ryan Sachire came in leading the head-to-head 1–0. Ryan Sachire extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-09-11 | USA 4 | R32 | hard | Ryan Sachire | 6-7(1) 7-5 6-2 |