Eric Drew defeated Lee Pearson 6-7 7-6 6-2 in the USA 2 Masters 4 round of 64 on hard. The upset overturned the form book — Lee Pearson came in leading the head-to-head 1–0. Eric Drew claimed a first win over Lee Pearson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 2 | R64 | hard | Lee Pearson | 6-3 6-2 |