Robert Kendrick defeated Michael Jessup 6-1 7-6 in the USA F21 round of 32 on hard. The upset overturned the form book — Michael Jessup came in leading the head-to-head 1–0. Robert Kendrick claimed a first win over Michael Jessup in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-11-27 | USA F29 | R32 | hard | Michael Jessup | 6-4 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.