Jesse Walter defeated John James 6-7 6-2 6-2 in the USA 3 Masters 1 semi-final on hard. The upset overturned the form book — John James came in leading the head-to-head 1–0. Jesse Walter claimed a first win over John James in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-09-11 | USA 3 Masters 2 | R16 | hard | John James | 2-6 6-3 6-4 |