Jon Goldfarb defeated Chad Rosser 6-4 6-3 in the Caribbean 1 Masters 2 round of 32 on hard. The upset overturned the form book — Chad Rosser came in leading the head-to-head 1–0. Jon Goldfarb claimed a first win over Chad Rosser in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-10-13 | USA 6 Masters 2 | R64 | hard | Chad Rosser | 6-7 6-4 6-4 |