Americo Venero Montes defeated Marcelo Rebolledo 7-5 6-1 in the Chile 1 Masters 4 qualifying round on clay. The result followed the form book — Americo Venero Montes came in leading the head-to-head 3–2. Americo Venero Montes extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-10-05 | Chile 2 Masters 1 | QF | clay | Americo Venero Montes | 6-2 6-2 |
| 1994-07-16 | Colombia Masters 1 | R16 | clay | Marcelo Rebolledo | 7-6 3-6 6-4 |
| 1993-08-15 | Ecuador Peru Masters 3 | SF | clay | Marcelo Rebolledo | 6-3 6-2 |
| 1993-08-15 | Ecuador Peru Masters 4 | QF | clay | Americo Venero Montes | 6-3 1-0 |
| 1991-09-23 | Ecuador Peru Masters 3 | R32 | clay | Americo Venero Montes | 3-6 6-3 6-4 |