Alexandre Simoni defeated Gabriel Keymer 6-1 6-1 in the Chile F1 semi-final on clay. The upset overturned the form book — Gabriel Keymer came in leading the head-to-head 2–0, but Alexandre Simoni had been the form player, winning 3 of their last 7 on clay. Alexandre Simoni claimed a first win over Gabriel Keymer in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | Chile F3 | R16 | clay | Gabriel Keymer | 6-3 2-6 6-4 |
| 1997-04-05 | Brazil 1 Masters 1 | R32 | clay | Gabriel Keymer | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.