Boris Bosnjakovic defeated Jeff Williams 6-7 7-6 6-4 in the USA 7 Masters 3 round of 16 on hard. The upset overturned the form book — Jeff Williams came in leading the head-to-head 1–0. Boris Bosnjakovic claimed a first win over Jeff Williams in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 1 | R16 | hard | Jeff Williams | 6-3 6-1 |