Kyle Rudman defeated Bobbie Altelaar 6-3 1-6 6-1 in the USA 3 Masters 1 round of 16 on hard. The upset overturned the form book — Bobbie Altelaar came in leading the head-to-head 1–0. Kyle Rudman claimed a first win over Bobbie Altelaar in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-10-16 | USA 4 Masters 1 | R64 | hard | Bobbie Altelaar | 7-5 6-4 |