Americo Venero Montes defeated Miguel Miranda 6-4 6-7 7-6 in the Chile 1 Masters 1 round of 32 on clay. The upset overturned the form book — Miguel Miranda came in leading the head-to-head 3–1. Americo Venero Montes narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-05-02 | Chile 2 Masters 4 | R16 | clay | Miguel Miranda | 6-3 7-6 |
| 1998-04-04 | Chile 1 Masters 2 | R16 | clay | Miguel Miranda | 6-4 3-6 7-5 |
| 1997-05-03 | Chile 1 Masters 3 | R16 | clay | Miguel Miranda | 0-6 7-6 6-4 |
| 1996-09-07 | Peru Bolivia Masters 4 | QF | clay | Americo Venero Montes | 7-6 4-6 6-4 |