Stadium: Hard 20 Round: 25 Ground: Hardcourt outdoor
| 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 Tbilisi | 2022/07/31 13:40 | Erik Arutiunian v Pavlos Tsitsipas | 6-2,6-2 |
| ITF M25 Tbilisi | 2022/07/31 06:00 | Irakli Tsurtsumia v Pavlos Tsitsipas | 5-7,3-6 |
| ITF M15 Heraklion | 2021/11/30 08:30 | Pavlos Tsitsipas v Harry Wendelken | 1-6,2-6 |
| ITF M15 Heraklion | 2021/11/21 11:00 | Pavlos Tsitsipas v Maxim Khorozov | 4-6,2-6 |
| ITF M15 Heraklion | 2023/11/21 07:00 | Lior Goldenberg v Gabriel Matuszewski | 7-6,6-7,10-5 |
| ITF M15 Heraklion | 2023/11/20 07:00 | Lior Goldenberg v Daniel Shemesh | 6-2,6-1 |
| ITF M15 Heraklion | 2023/11/15 10:50 | Lior Goldenberg v Gianmarco Ferrari | 5-7,2-6 |
| ITF M25 Heraklion | 2023/11/14 07:30 | Lior Goldenberg v Max Cunat | 1-6,7-5,10-7 |
| ITF M25 Heraklion | 2023/11/12 12:00 | Lior Goldenberg v Stephanos Schinas | 6-0,6-4 |
| ITF M25 Heraklion | 2023/11/06 07:00 | Dimitris Sakellaridis v Lior Goldenberg | 6-3,6-4 |
| ITF M25 Heraklion | 2023/11/05 09:00 | Thomas Sorensen v Lior Goldenberg | 2-6,3-6 |
| ITF M25 Heraklion | 2023/11/01 10:00 | Laurent Lokoli v Lior Goldenberg | 6-3,6-0 |