Sam Ryan Ziegann defeated Hugh Winter 6-0 6-3 in the M15 Brisbane 1 round of 32 on hard. Sam Ryan Ziegann extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-05-18 | M15 Heraklion 6 | Q64 | hard | Hugh Winter | 6-4 6-2 |
| 2022-02-06 | M25 Canberra 1 | Q32 | hard | Sam Ryan Ziegann | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.