Claudio Grassi defeated Damiano Di Ienno 6-2 6-0 in the Serbia F5 qualifying round on clay. Claudio Grassi extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2012-03-19 | Italy F1 | R16 | hard | Claudio Grassi | 6-3 6-2 |
| 2007-08-27 | Croatia F8 | R32 | clay | Damiano Di Ienno | 6-2 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.