Stadium: Court 16 Round: 44 Ground: Hardcourt outdoor
| ITF M15 Heraklion | 2023/10/16 09:00 | Gianluca Carlini v Gabriel Matuszewski | 6-4,1-6,5-10 |
| ITF M15 Heraklion | 2023/10/23 09:00 | Jonas Trinker v Gianluca Carlini | 6-3,6-4 |
| ITF M15 Heraklion | 2023/10/22 08:30 | Oskar Grzegorzewski v Gianluca Carlini | 4-6,4-6 |
| ITF M15 Heraklion | 2023/10/16 09:00 | Gianluca Carlini v Gabriel Matuszewski | 6-4,1-6,5-10 |
| ITF M15 Monastir | 2023/09/25 12:30 | Ludovico Vaccari v Gianluca Carlini | 6-4,6-4 |
| ITF M15 Monastir | 2023/09/25 08:30 | Samyar Elyasi v Gianluca Carlini | 0-6,1-6 |
| ITF M15 Monastir | 2023/09/24 08:30 | Gianluca Carlini v Enmanuel Munoz | 3-6,6-3,10-3 |
| ITF M15 Monastir | 2023/09/18 12:30 | Keshav Chopra v Gianluca Carlini | 4-6,6-1,10-5 |
| ITF M15 Monastir | 2023/09/18 08:00 | Gianluca Carlini v Shivank Bhatnagar | 7-5,6-0 |
| ITF M15 Heraklion | 2023/10/22 08:30 | Gabriel Matuszewski v Stefan Cizelj-Zivkovic | 4-6,4-6 |
| ITF M15 Heraklion | 2023/10/17 06:30 | Ioannis Kountourakis v Gabriel Matuszewski | 6-3,6-0 |
| ITF M15 Heraklion | 2023/10/16 09:00 | Gianluca Carlini v Gabriel Matuszewski | 6-4,1-6,5-10 |
| UTR Pro Beograd | 2023/10/12 07:30 | Aleksa Mardjonovic v Gabriel Matuszewski | 0-3 |
| UTR Pro Beograd | 2023/10/10 12:58 | Gabriel Matuszewski v Drazen Petrovic | 6-3,6-4 |
| UTR Pro Beograd | 2023/10/08 09:00 | Gabriel Matuszewski v Vuk Radjenovic | 2-6,5-7 |
| UTR Pro Beograd | 2023/10/07 08:07 | Gabriel Matuszewski v Tadija Radovanovic | 5-7,6-4,5-7 |
| UTR Pro Beograd | 2023/10/05 06:00 | Luka Todorovic v Gabriel Matuszewski | 0-0 |