Jamie Holmes defeated Mike Chinchiolo 7-6 7-5 in the USA 2 Masters 4 round of 16 on hard. The result followed the form book — Jamie Holmes came in leading the head-to-head 1–0. Jamie Holmes extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-06-09 | USA 3 Masters 2 | R32 | hard | Jamie Holmes | 6-4 7-5 |