Miguel Miranda defeated Gabriel Keymer 7-5 6-4 in the Chile 1 Masters 3 semi-final on clay. The upset overturned the form book — Gabriel Keymer came in leading the head-to-head 2–0, but Miguel Miranda had been the form player, winning 4 of their last 8 on clay. Miguel Miranda 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 | R32 | clay | Gabriel Keymer | 6-0 6-4 |
| 1998-11-16 | Chile F1 | R16 | clay | Gabriel Keymer | 6-0 6-7 6-0 |