Pablo Santos defeated Guillermo Olaso 4-6 6-4 6-1 in the Spain F7 round of 16 on clay. Pablo Santos extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-10-25 | Spain F38 | F | clay | Guillermo Olaso | 6-2 7-5 |
| 2010-08-30 | Spain F31 | SF | clay | Guillermo Olaso | 7-5 6-4 |
| 2010-03-15 | Spain F9 | SF | clay | Pablo Santos | 7-6(9) 7-6(5) |
| 2008-07-07 | Italy F21 | F | clay | Pablo Santos | 6-0 |
| 2007-07-16 | Spain F27 | F | clay | Guillermo Olaso | 6-4 6-4 |
| 2007-04-30 | Spain F16 | R32 | clay | Pablo Santos | 4-6 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.