Ground: Hardcourt outdoor
| 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 M25 Caloundra | 2024/11/23 01:10 | Sam Ryan Ziegann v Edward Winter | 3-6,4-6 |
| ITF M25 Caloundra | 2024/11/19 01:35 | James Watt v Edward Winter | 3-6,6-4,4-6 |
| Challenger Sydney | 2024/10/28 23:00 | Marc Polmans v Edward Winter | 6-2,6-2 |
| ITF M15 Lannion | 2025/02/21 10:30 | Hamish Stewart v Olaf Pieczkowski | 6-2,6-4 |
| ITF M15 Lannion | 2025/02/20 10:30 | Nicolas Ifi v Olaf Pieczkowski | 5-7,5-7 |
| ITF M15 Lannion | 2025/02/19 14:30 | Dorian Tremblay v Olaf Pieczkowski | 3-6,2-6 |
| Challenger New Delhi | 2025/02/09 05:00 | Sascha Gueymard Wayenburg v Olaf Pieczkowski | 6-1,6-1 |
| Challenger Chennai | 2025/02/03 05:40 | Hynek Barton v Olaf Pieczkowski | 6-3,6-3 |
| Challenger Chennai | 2025/02/02 07:10 | Bharath Nishok Kumaran v Olaf Pieczkowski | 6-7,0-6 |
| ITF M15 Monastir | 2025/01/16 08:30 | Olaf Pieczkowski v Niklas Waldner | 4-6,0-1 |
| ITF M15 Oslo | 2025/01/11 10:00 | Tom Paris v Olaf Pieczkowski | 6-7,5-7 |