Stadium: Court 16 Round: 44 Ground: Hardcourt outdoor
| ITF - M15 Héraklion | 2023/10/16 09:00 | Ioannis Kountourakis v Piotr Siekanowicz | 6-3,6-0 |
| ITF - M15 Kursumlijska Banja | 2023/09/21 12:30 | Ioannis Kountourakis v Stefan Popovic | 2-6,4-6 |
| ITF - M15 Kursumlijska Banja | 2023/09/20 11:25 | Milan Drinic v Ioannis Kountourakis | 4-6,6-3,4-6 |
| ITF - M15 Kursumlijska Banja | 2023/09/19 08:45 | Marko Nikolic v Ioannis Kountourakis | 4-6,4-6 |
| ITF - M15 Kursumlijska Banja | 2023/09/18 11:00 | Aleksandar Mihailovic v Ioannis Kountourakis | 1-6,6-7 |
| ITF - M15 Kursumlijska Banja | 2023/09/13 11:35 | Vlad Andrei Dancu v Ioannis Kountourakis | 6-3,6-4 |
| ITF - M15 Kursumlijska Banja | 2023/09/12 07:00 | Antonio Massara v Ioannis Kountourakis | 6-7,4-6 |
| ITF - M15 Kursumlijska Banja | 2023/09/11 09:30 | Ioannis Kountourakis v Iamachkine, Pedro | 6-4,6-1 |
| ITF - M15 Héraklion | 2023/10/16 09:00 | Gianluca Carlini v Gabriel Matuszewski | 6-4,1-6,5-10 |
| UTR - Série Pro - Beograd | 2023/10/12 07:30 | Aleksa Mardjonovic v Gabriel Matuszewski | 0-3 |
| UTR - Série Pro - Beograd | 2023/10/10 12:58 | Gabriel Matuszewski v Drazen Petrovic | 6-3,6-4 |
| UTR - Série Pro - Beograd | 2023/10/08 09:00 | Gabriel Matuszewski v Vuk Radjenovic | 2-6,5-7 |
| UTR - Série Pro - Beograd | 2023/10/07 08:07 | Gabriel Matuszewski v Tadija Radovanovic | 5-7,6-4,5-7 |
| UTR - Série Pro - Beograd | 2023/10/05 06:00 | Luka Todorovic v Gabriel Matuszewski | 0-0 |
| UTR - Série Pro - Beograd | 2023/10/04 06:00 | Gabriel Matuszewski v Illya Beloborodko | 0-6,6-1,4-6 |
| UTR - Série Pro - Beograd | 2023/10/02 12:13 | Gabriel Matuszewski v Oleg Prihodko | 2-6,4-6 |