Tate Roberts defeated Joseph Sirianni 6-3 6-4 in the Australia 3 Masters 2 round of 32 on hard. The upset overturned the form book — Joseph Sirianni came in leading the head-to-head 1–0. Tate Roberts claimed a first win over Joseph Sirianni in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-08 | Australia 2 Masters 2 | R32 | hard | Joseph Sirianni | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.