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