Ground: Hardcourt outdoor
| ITF M25 Calabasas | 2025/03/27 20:32 | Strong Kirchheimer v Edward Winter | 7-6,6-4 |
| ITF M25 Calabasas | 2025/03/25 20:40 | Edward Winter v Charles Broom | 7-6,7-6 |
| ITF M15 Sherbrooke | 2025/03/05 19:00 | Edward Winter v Daniel Milavsky | 7-6,4-6,4-5 |
| Australian Open | 2025/01/07 06:25 | Edward Winter v Carlos Taberner | 4-6,5-7 |
| Challenger Canberra | 2024/12/29 23:30 | Edward Winter v Hady Habib | 4-6,4-6 |
| Challenger Canberra | 2024/12/28 23:30 | Pierre-Hugues Herbert v Edward Winter | 1-6,2-6 |
| ITF M25 Carrara | 2024/11/26 02:45 | Edward Winter v Jason Kubler | 4-6,4-6 |
| ITF M25 Caloundra | 2024/11/24 00:00 | Edward Winter v Matthew Dellavedova | 6-1,4-6,10-12 |
| ITF M15 Heraklion | 2025/04/05 07:30 | Olaf Pieczkowski v Stuart Parker | 6-3,3-6,2-6 |
| ITF M15 Heraklion | 2025/04/04 08:30 | Olaf Pieczkowski v Leonardo Rossi | 4-4 |
| ITF M15 Heraklion | 2025/04/03 10:38 | Olaf Pieczkowski v Leyton Rivera | 4-6,6-3,6-4 |
| ITF M15 Heraklion | 2025/04/02 16:26 | Olaf Pieczkowski v Dominick Mosejczuk | 6-2,7-5 |
| ITF M15 Heraklion | 2025/03/27 07:30 | Amit Vales v Olaf Pieczkowski | 6-3,6-4 |
| ITF M15 Heraklion | 2025/03/26 07:30 | Andrin Casanova v Olaf Pieczkowski | 3-6,6-4,4-6 |
| ITF M15 Sharm El Sheikh | 2025/03/13 08:00 | Olaf Pieczkowski v Michele Ribecai | 2-6,2-6 |
| ITF M15 Sharm El Sheikh | 2025/03/05 09:30 | Kristjan Tamm v Olaf Pieczkowski | 6-1,6-4 |