Sule Ladipo defeated Chris Pressley 6-0 6-2 in the USA 2 Masters 4 semi-final on clay. The upset overturned the form book — Chris Pressley came in leading the head-to-head 1–0. Sule Ladipo claimed a first win over Chris Pressley in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1993-07-09 | USA 4 Masters 2 | R16 | hard | Chris Pressley | 6-1 4-6 6-3 |