Grega Zemlja advanced when Bostjan Osabnik retired 6-4 in the Austria F2 round of 32. Grega Zemlja narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-11-22 | Tunisia F5 | R16 | hard | Bostjan Osabnik | 7-6(2) 6-4 |
| 2004-10-25 | Czech Rep F4 | R16 | hard | Bostjan Osabnik | 6-1 7-5 |
| 2004-06-07 | Slovenia F2 | SF | clay | Grega Zemlja | 6-4 6-0 |
| 2003-06-02 | Slovenia F1 | R32 | clay | Bostjan Osabnik | 7-5 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.