Silvio Scaiola advanced when Gabriel Silberstein retired 4-1 in the Chile 2 Masters 2 qualifying round. Silvio Scaiola claimed a first win over Gabriel Silberstein in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-10-05 | Chile 2 Masters 3 | SF | clay | Gabriel Silberstein | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.