Stadium: Court 3 Round: 62 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/27 10:00 | Christos Glavas v Ewan Moore | 5-7,1-6 |
| ITF M15 Heraklion | 2023/11/14 08:30 | Amit Vales v Christos Glavas | 6-1,6-4 |
| ITF M25 Heraklion | 2023/11/08 11:35 | Christos Glavas v Sebastian Gima | 2-6,6-7 |
| ITF M25 Heraklion | 2023/10/29 12:45 | Lech Gontar v Christos Glavas | 2-6,4-6 |
| ITF M15 Heraklion | 2023/10/22 06:00 | Christos Glavas v Alessandro Spadola | 2-6,1-6 |
| UTR Pro Thessaloniki | 2023/04/30 05:00 | Christos Glavas v Besir Durguti | 6-3,3-2 |
| UTR Pro Thessaloniki | 2023/04/29 08:24 | Michalis Sakellaridis v Christos Glavas | 0-3 |
| ITF M15 Koszalin | 2023/09/04 07:30 | Juliusz Bienkiewicz v Kacper Szymkowiak | 6-2,7-5 |
| ITF M15 Szczawno | 2023/08/27 09:30 | Kacper Szymkowiak v Mikolaj Borkowski | 7-5,6-7,7-10 |
| ITF M25 Poznan | 2023/08/20 13:30 | Andrea Meduri v Kacper Szymkowiak | 6-4,6-2 |
| ITF M25 Bielsko Biala | 2023/08/14 07:30 | Siim Troost v Kacper Szymkowiak | 7-5,6-4 |
| ITF M25 Lodz | 2023/08/08 09:00 | Marcel Kamrowski v Kacper Szymkowiak | 6-4,7-5 |
| ITF M25 Lodz | 2023/08/07 13:30 | Dimitris Sakellaridis v Kacper Szymkowiak | 4-6,3-6 |
| ITF M25 Lodz | 2023/08/07 07:30 | Kacper Szymkowiak v Aliaksey Matsiush | 6-1,6-1 |
| ITF M15 Wroclaw | 2023/06/25 08:00 | Michael Minasyan v Kacper Szymkowiak | 6-4,1-6,1-10 |