Stadium: Hard 20 Round: 62 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/10/30 09:30 | Guy Den Heijer v Gabriel Matuszewski | 6-1,6-4 |
| ITF M25 Heraklion | 2023/10/29 10:30 | Gianluca Carlini v Gabriel Matuszewski | 6-7,1-6 |
| 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 |
| ITF M25 Santa Margherita | 2023/10/01 08:30 | Pietro Marino v Mattia Ricci | 6-1,6-1 |
| ITF M15 Monastir | 2023/09/24 10:30 | Timothe Barthes v Mattia Ricci | 6-4,3-6,10-6 |
| ITF M25 Pozzuoli | 2023/09/11 09:00 | Filippo Mazzola v Mattia Ricci | 6-7,7-6,10-7 |
| ITF M25 Pozzuoli | 2023/09/10 07:45 | Mattia Ricci v Benito Massacri | 7-5,6-1 |
| ITF M15 Koszalin | 2023/09/03 09:00 | Alexander C Parker v Mattia Ricci | 6-2,2-6,10-7 |