Eric Drew defeated Rafael De Mesa 6-3 6-4 in the USA 4 Masters 2 qualifying round on hard. The upset overturned the form book — Rafael De Mesa came in leading the head-to-head 1–0. Eric Drew claimed a first win over Rafael De Mesa in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-10-16 | USA 4 Masters 3 | R16 | hard | Rafael De Mesa | 2-6 6-3 6-3 |