Stadium: Court 3 Round: 54 Ground: Clay
| 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 |