Sam Schroerlucke defeated Michael Jessup 5-7 6-1 7-6 in the Mexico 1 Masters 1 round of 16 on hard. The result followed the form book — Sam Schroerlucke came in leading the head-to-head 1–0. Sam Schroerlucke extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-24 | Mexico 1 Masters 2 | R32 | hard | Sam Schroerlucke | 4-6 7-6 7-5 |