Wynn Criswell defeated Jonathan Pastel 4-6 6-4 6-1 in the USA 2 Masters 4 qualifying round on hard. The result followed the form book — Wynn Criswell came in leading the head-to-head 1–0. Wynn Criswell extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | Canada F1 | R32 | hard | Wynn Criswell | 6-4 6-4 |