Mitch Sprengelmeyer advanced when Andrew Rueb retired 3-0 in the USA 5 Masters 3 round of 64. Mitch Sprengelmeyer claimed a first win over Andrew Rueb in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-26 | USA 1 Masters 3 | R64 | hard | Andrew Rueb | 6-4 7-5 |