Leonardo Tavares defeated Guillermo Olaso 6-4 4-6 6-4 in the Portugal F4 qualifying round on hard. The upset overturned the form book — Guillermo Olaso came in leading the head-to-head 2–1. Leonardo Tavares narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-10-06 | Portugal F8 | R16 | clay | Leonardo Tavares | 6-0 7-5 |
| 2008-04-21 | Spain F16 | R32 | clay | Guillermo Olaso | 2-6 6-4 6-3 |
| 2008-03-31 | Spain F13 | R32 | clay | Guillermo Olaso | 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.