Juan Robinson Gamonal defeated Sergio Cortes 4-6 7-5 7-6 in the Chile 1 Masters 2 qualifying round on clay. The upset overturned the form book — Sergio Cortes came in leading the head-to-head 3–0. Juan Robinson Gamonal claimed a first win over Sergio Cortes in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-10-05 | Chile 2 Masters 4 | R32 | clay | Sergio Cortes | 6-3 7-5 |
| 1996-03-23 | Chile 1 Masters 4 | R16 | clay | Sergio Cortes | 4-6 6-1 7-6 |
| 1995-09-30 | Chile Masters 3 | R32 | clay | Sergio Cortes | 6-2 6-1 |