Dmitry Tursunov defeated Eric Drew 7-6 4-6 6-2 in the USA F18 qualifying round on hard. The upset overturned the form book — Eric Drew came in leading the head-to-head 1–0, but Dmitry Tursunov had been the form player, winning 3 of their last 4 on hard. Dmitry Tursunov claimed a first win over Eric Drew in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | USA F17 | R16 | hard | Eric Drew | 6-4 4-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.