Matthew Barton defeated Andrew Gregory 4-6 6-3 6-4 in the Australia F5 round of 32 on hard. The upset overturned the form book — Andrew Gregory came in leading the head-to-head 1–0. Matthew Barton claimed a first win over Andrew Gregory in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-10-13 | Australia F9 | R32 | clay | Andrew Gregory | 6-0 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.