Rodrigo Cerdera defeated Gabriel Keymer 6-2 6-1 in the Chile F6 round of 32 on clay. The upset overturned the form book — Gabriel Keymer came in leading the head-to-head 2–0, but Rodrigo Cerdera had been the form player, winning 5 of their last 10 on clay. Rodrigo Cerdera claimed a first win over Gabriel Keymer in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-10 | Chile F1 | R16 | clay | Gabriel Keymer | 5-7 6-3 6-2 |
| 1997-05-03 | Chile 1 Masters 3 | QF | clay | Gabriel Keymer | 7-5 6-4 |