Christopher Kas advanced when Matteo Colla retired 7-6 3-0 in the Italy 3 1 qualifying round. Christopher Kas narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-05-12 | Italy F7 | R16 | clay | Matteo Colla | 6-1 7-6(7) |
| 2001-08-20 | Italy 4 4 | SF | clay | Matteo Colla | 6-1 2-6 7-5 |
| 2000-09-18 | Italy F11 | R16 | hard | Christopher Kas | 7-5 5-7 6-4 |