Oren Motevassel defeated Chris Pressley 6-3 7-6 in the USA 4 Masters 1 round of 16 on hard. Oren Motevassel extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-09-06 | USA 5 Masters 4 | F | hard | Oren Motevassel | 5-7 6-2 6-0 |
| 1995-07-07 | USA 4 Masters 4 | QF | hard | Chris Pressley | 6-2 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.