Stadium: Centre Court Round: 25 Ground: Hardcourt outdoor
| Challenger Perugia | 2025/06/08 08:00 | Luca Castagnola v Marco Cecchinato | 3-6,3-6 |
| ITF M15 Ljubljana | 2025/06/05 09:30 | Luca Castagnola v Valentin Basel | 4-6,0-6 |
| Challenger Vicenza | 2025/05/28 12:00 | Luca Castagnola v Ignacio Buse | 3-6,2-6 |
| Challenger Vicenza | 2025/05/27 14:00 | Luka Pavlovic v Luca Castagnola | 4-6,6-4,5-7 |
| ITF M15 Brcko | 2025/05/24 09:30 | Dusan Obradovic v Luca Castagnola | 3-6,6-4,7-5 |
| ITF M15 Brcko | 2025/05/24 07:00 | Luca Castagnola v Maximilian Homberg | 6-2,2-6,6-3 |
| ITF M15 Brcko | 2025/05/22 09:00 | Luca Castagnola v Luca Fantini | 6-1,6-2 |
| ITF M15 Brcko | 2025/05/21 13:02 | Luca Castagnola v Aljaz Jeran | 6-2,6-4 |
| UTR Pro Glifada | 2025/06/06 09:45 | Pavlos Tsitsipas v Vadym Konovchuk | 6-7,3-6 |
| UTR Pro Glifada | 2025/06/04 06:00 | Pavlos Tsitsipas v Constantinos Djakouris | 6-3,6-4 |
| UTR Pro Glifada | 2025/06/03 09:25 | Pavlos Tsitsipas v Michalis Sakellaridis | 3-6,6-3,6-4 |
| UTR Pro Glifada | 2025/06/02 14:10 | Adamantios Stavrakas v Pavlos Tsitsipas | 6-1,4-6,6-3 |
| ITF M25 Heraklion | 2025/05/29 14:02 | Fabrizio Andaloro v Pavlos Tsitsipas | 6-3,6-3 |
| ITF M25 Heraklion | 2025/05/28 13:52 | Pavlos Tsitsipas v Gabriel Matuszewski | 6-2,1-6,7-6 |
| Challenger Tbilisi | 2025/05/18 10:30 | Pavlos Tsitsipas v Sergey Fomin | 3-6,5-7 |
| ITF M15 Heraklion | 2025/05/14 08:30 | Alfredo Perez v Pavlos Tsitsipas | 6-2,6-3 |