Joseph Sirianni defeated Luka Gregorc 3-6 7-6 7-6 in the New Haven q32 on hard. The result followed the form book — Joseph Sirianni came in leading the head-to-head 2–1. Joseph Sirianni extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-18 | Wimbledon | Q32 | grass | Luka Gregorc | 6-4 6-4 7-5 |
| 2003-03-24 | Australia F1 | R32 | hard | Joseph Sirianni | 4-6 6-2 7-6(4) |
| 2002-09-23 | Australia 2 3 | R16 | hard | Joseph Sirianni | 6-3 7-6(1) |