Doug Root defeated Lee Pearson 6-2 6-4 in the USA 2 Masters 1 round of 32 on hard. The upset overturned the form book — Lee Pearson came in leading the head-to-head 1–0. Doug Root claimed a first win over Lee Pearson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-07-19 | USA 4 Masters 4 | R64 | hard | Lee Pearson | 6-2 7-6 |