Stadium: Centre Court Round: 14 Ground: Hardcourt outdoor
| Challenger Chisinau | 2025/05/26 13:25 | Maximus Jones v Olaf Pieczkowski | 2-6,2-6 |
| Challenger Chisinau | 2025/05/25 13:55 | Daniel Uta v Olaf Pieczkowski | 3-6,2-6 |
| Challenger Tbilisi | 2025/05/18 11:55 | Olaf Pieczkowski v Ajeet Rai | 6-4,5-7,0-6 |
| ITF M15 Monastir | 2025/04/27 09:00 | Tuncay Duran v Olaf Pieczkowski | 5-7,4-6 |
| ITF M15 Monastir | 2025/04/26 09:00 | Buvaysar Gadamauri v Olaf Pieczkowski | 4-6,5-7 |
| ITF M15 Monastir | 2025/04/25 08:30 | Olaf Pieczkowski v Mert Alkaya | 6-2,6-4 |
| ITF M15 Monastir | 2025/04/24 10:00 | Olaf Pieczkowski v Matthew Summers | 6-3,6-2 |
| ITF M15 Monastir | 2025/04/23 10:38 | Olaf Pieczkowski v Alaa Trifi | 7-5,6-4 |
| ITF M15 Heraklion | 2025/05/22 07:01 | Fares Zakaria v Dimitris Sakellaridis | 6-4,6-1 |
| ITF M15 Heraklion | 2025/05/21 11:30 | Joao Victor C Loureiro v Dimitris Sakellaridis | 3-6,3-6 |
| ITF M15 Heraklion | 2025/05/14 07:00 | Stylianos Christodoulou v Dimitris Sakellaridis | 6-4,6-2 |
| ITF M15 Heraklion | 2025/05/09 09:30 | Dimitris Sakellaridis v Ivan Marrero Curbelo | 6-7,3-5 |
| ITF M15 Heraklion | 2025/05/08 07:00 | Dimitris Sakellaridis v Andreas Timini | 6-1,6-3 |
| ITF M15 Heraklion | 2025/05/07 11:10 | Amit Vales v Dimitris Sakellaridis | 4-6,4-6 |
| ITF M15 Monastir | 2025/05/01 10:00 | Dimitris Sakellaridis v Etienne Donnet | 7-6,6-3 |
| ITF M15 Monastir | 2025/04/30 08:30 | Peter Buldorini v Dimitris Sakellaridis | 5-7,0-2 |