Eric Drew defeated Masahide Sakamoto 4-6 6-2 6-4 in the USA F12 round of 64 on hard. The result followed the form book — Eric Drew came in leading the head-to-head 1–0. Eric Drew extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 4 | R32 | hard | Eric Drew | 7-5 6-3 |