Lesley Joseph defeated Scott Lipsky 7-5 6-3 in the USA F28 round of 32 on hard. The upset overturned the form book — Scott Lipsky came in leading the head-to-head 2–0, but Lesley Joseph had been the form player, winning 7 of their last 10 on hard. Lesley Joseph claimed a first win over Scott Lipsky in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-06-26 | USA F14 | R16 | hard | Scott Lipsky | 7-5 6-7(12) 6-4 |
| 2004-06-07 | USA F13 | QF | hard | Scott Lipsky | 7-6(2) 7-6(2) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.