Borja Malo defeated Alejandro Kon 6-2 6-7 6-4 in the Chile F1 qualifying round on clay. The upset overturned the form book — Alejandro Kon came in leading the head-to-head 1–0. Borja Malo claimed a first win over Alejandro Kon in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-05 | Colombia F4 | R16 | clay | Alejandro Kon | 6-2 6-1 |