Alex Theiler defeated Agustin Picco 6-2 6-3 in the Bolivia F3 round of 16 on clay. The upset overturned the form book — Agustin Picco came in leading the head-to-head 1–0. Alex Theiler claimed a first win over Agustin Picco in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-10-19 | Chile F3 | R32 | clay | Agustin Picco | 5-7 7-5 5-3 |