Chris Pressley defeated Glenn Weiner 7-5 5-7 6-3 in the USA 1 Masters 1 semi-final on hard. The result followed the form book — Chris Pressley came in leading the head-to-head 1–0. Chris Pressley extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-09-06 | USA 5 Masters 1 | SF | hard | Chris Pressley | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.