Federico Dondo defeated Oscar Bustos 6-4 6-3 in the Chile F2 semi-final on clay. The result followed the form book — Federico Dondo came in leading the head-to-head 1–0. Federico Dondo extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | Netherlands Masters 4 | R16 | clay | Federico Dondo | 1-6 7-6 6-3 |