Robert Kendrick defeated Jeff Williams 6-2 6-2 in the Scottsdale q32 on hard. The upset overturned the form book — Jeff Williams came in leading the head-to-head 3–0. Robert Kendrick claimed a first win over Jeff Williams in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 1 | SF | hard | Jeff Williams | 7-6 6-4 |
| 1999-07-26 | USA F12 | R32 | hard | Jeff Williams | 2-6 6-3 6-4 |
| 1999-06-21 | USA F8 | R32 | hard | Jeff Williams | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.