Michael Jessup defeated Robert Kendrick 6-4 7-5 in the USA F29 round of 32 on hard. The upset overturned the form book — Robert Kendrick came in leading the head-to-head 1–0, but Michael Jessup had been the form player, winning 2 of their last 5 on hard. Michael Jessup claimed a first win over Robert Kendrick in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-29 | USA F21 | R32 | hard | Robert Kendrick | 6-1 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.