Hans Podlipnik Castillo advanced when Guillermo Hormazabal retired 5-7 3-2 in the Italy F21 round of 32. Hans Podlipnik Castillo narrowed the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2011-10-10 | Chile F8 | F | clay | Guillermo Hormazabal | 6-2 6-1 |
| 2010-11-22 | Chile F6 | QF | clay | Guillermo Hormazabal | 7-5 6-1 |
| 2008-07-21 | Italy F23 | R16 | clay | Hans Podlipnik Castillo | 6-4 6-2 |
| 2008-06-02 | Poland F4 | R32 | clay | Guillermo Hormazabal | 6-3 6-4 |
| 2008-05-26 | Poland F3 | R16 | clay | Hans Podlipnik Castillo | 6-3 6-2 |
| 2007-03-19 | Ghana F2 | R32 | clay | Guillermo Hormazabal | 5-7 6-1 6-2 |
| 2007-03-05 | Nigeria F2 | QF | hard | Guillermo Hormazabal | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.