Thomas Schiessling defeated Elia Grossi 6-4 3-6 7-6 in the Italy F5 qualifying round on clay. Thomas Schiessling extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-05-20 | Italy F3 | R32 | clay | Elia Grossi | 6-2 4-0 |
| 2000-05-29 | Italy F4 | F | clay | Thomas Schiessling | 2-6 7-6(4) 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.