Diego Moyano defeated Rodolfo Rake 6-1 7-5 in the Chile F5 semi-final on clay. The result followed the form book — Diego Moyano came in leading the head-to-head 1–0. Diego Moyano extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | Chile F4 | R16 | clay | Diego Moyano | 6-4 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.