Ashwin Ryan Sharma defeated Winter Meagher 6-4 6-4 in the M25 Toowoomba 1 q64 on hard. The upset overturned the form book — Winter Meagher came in leading the head-to-head 1–0. Ashwin Ryan Sharma claimed a first win over Winter Meagher in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-03-25 | M15 Mornington 2 | Q32 | clay | Winter Meagher | 6-3 4-6 10-5 |