Franco Squillari defeated Diego Del Rio 1-6 6-4 6-2 in the Chile Masters 1 final on clay. The upset overturned the form book — Diego Del Rio came in leading the head-to-head 8–1, but Franco Squillari had been the form player, winning 5 of their last 7 on clay. Franco Squillari narrowed the head-to-head to 8–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-09-30 | Argentina 3 Masters 1 | F | clay | Diego Del Rio | 7-6 6-7 6-4 |
| 1995-09-02 | Argentina 2 Masters 4 | R32 | clay | Diego Del Rio | 7-5 6-1 |
| 1995-04-01 | Argentina 1 Masters 4 | R32 | clay | Franco Squillari | 3-6 7-5 6-3 |
| 1994-07-16 | Argentina 2 Masters 3 | F | clay | Diego Del Rio | 6-1 6-3 |
| 1993-08-14 | Argentina 3 Masters 1 | R16 | clay | Diego Del Rio | 6-3 6-2 |
| 1992-08-10 | Argentina 2 Masters 4 | QF | clay | Diego Del Rio | 6-3 7-5 |
| 1992-08-10 | Argentina 2 Masters 3 | R16 | clay | Diego Del Rio | 6-2 6-2 |
| 1991-09-02 | Brazil 6 Masters 3 | F | clay | Diego Del Rio | 7-6 6-2 |
| 1991-05-13 | Brazil 3 Masters 4 | R32 | clay | Diego Del Rio | 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.