Mariano Zabaleta defeated Diego Hartfield 0-6 6-4 7-6 in the Vina del Mar q16 on clay. The upset overturned the form book — Diego Hartfield came in leading the head-to-head 1–0, defending last year's round of 16. Mariano Zabaleta claimed a first win over Diego Hartfield in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-01-28 | Vina del Mar | R32 | clay | Diego Hartfield | 6-3 7-5 |