Stadium: Center Court Round: 19 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/12/01 10:50 | Pavlos Tsitsipas v Marek Gengel | 6-3,2-6,2-6 |
| ITF M25 Heraklion | 2023/11/30 13:00 | Pavlos Tsitsipas v Filip Krolo | 3-6,6-1,6-4 |
| ITF M15 Heraklion | 2023/11/23 10:00 | Pavlos Tsitsipas v Rodrigo Alujas | 3-6,6-2,4-6 |
| ITF M15 Heraklion | 2023/11/22 13:05 | Pavlos Tsitsipas v Lior Goldenberg | 6-2,7-6 |
| ITF M25 Heraklion | 2023/10/31 09:00 | Marlon Vankan v Pavlos Tsitsipas | 6-4,6-4 |
| ITF M15 Heraklion | 2023/10/24 06:30 | Stefan Palosi v Pavlos Tsitsipas | 6-4,6-7,10-7 |
| ITF M15 Heraklion | 2023/10/23 06:30 | Pavlos Tsitsipas v Daniele Rapagnetta | 7-5,6-3 |
| ITF M15 Heraklion | 2023/10/17 09:00 | Stefan Palosi v Pavlos Tsitsipas | 6-4,6-2 |
| ITF M25 Monastir | 2023/11/15 12:25 | Nikolay Vylegzhanin v Robert Strombachs | 6-4,3-6,3-6 |
| ITF M25 Monastir | 2023/11/11 09:00 | Clement Tabur v Nikolay Vylegzhanin | 6-1,6-2 |
| ITF M25 Monastir | 2023/11/10 10:30 | Eliakim Coulibaly v Nikolay Vylegzhanin | 5-7,4-6 |
| ITF M25 Monastir | 2023/11/09 11:55 | Patrick Schoen v Nikolay Vylegzhanin | 3-6,5-7 |
| ITF M25 Monastir | 2023/11/08 11:25 | Rayen Hermassi v Nikolay Vylegzhanin | 2-6,1-6 |
| ITF M25 Mulhouse | 2023/11/03 11:50 | Nikolay Vylegzhanin v Lucas Poullain | 1-6,0-6 |
| ITF M25 Mulhouse | 2023/11/02 11:35 | Max Dahlin v Nikolay Vylegzhanin | 4-6,5-7 |
| ITF M25 Mulhouse | 2023/11/01 14:35 | Antoine Hoang v Nikolay Vylegzhanin | 2-6,2-6 |