Oliver Johl defeated Chris Pressley 6-4 6-4 in the USA 2 Masters 2 round of 16 on clay. The upset overturned the form book — Chris Pressley came in leading the head-to-head 3–0. Oliver Johl claimed a first win over Chris Pressley in four meetings, narrowing 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 4 | QF | clay | Chris Pressley | 6-3 6-2 |
| 1995-07-07 | USA 4 Masters 2 | SF | hard | Chris Pressley | 6-4 6-2 |