Jeff Williams advanced when Dmitry Tursunov retired 3-5 4-1 1-0 in the USA F21 semi-final. Jeff Williams narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-03-03 | Scottsdale | Q16 | hard | Dmitry Tursunov | 6-4 6-4 |
| 1999-07-05 | USA F10 | R32 | hard | Dmitry Tursunov | 6-4 6-4 |
| 1999-06-14 | USA F7 | R64 | hard | Jeff Williams | 7-5 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.