Chris Pressley defeated Oliver Johl 6-3 6-2 in the USA 2 Masters 4 qualifying round on clay. The result followed the form book — Chris Pressley came in leading the head-to-head 2–1. Chris Pressley extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-10-11 | USA 6 Masters 3 | R32 | hard | Chris Pressley | 6-2 6-3 |
| 1996-05-17 | USA 2 Masters 2 | R16 | clay | Oliver Johl | 6-4 6-4 |
| 1995-07-07 | USA 4 Masters 2 | SF | hard | Chris Pressley | 6-4 6-2 |