Stadium: Center Court Round: 26 Ground: Hardcourt outdoor
| 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 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 M25 Heraklion | 2023/11/29 09:10 | Filip Krolo v David Mizrahi | 6-4,6-7,7-6 |
| ITF M15 Heraklion | 2023/11/20 07:00 | Filip Krolo v Przemyslaw Michocki | 3-6,6-2,7-10 |
| ITF M25 Heraklion | 2023/11/12 12:00 | Jannik Maute v Filip Krolo | 6-1,7-5 |
| UTR Pro Zadar | 2023/10/22 12:35 | Janos Fekete v Filip Krolo | 6-1,6-3 |
| UTR Pro Zadar | 2023/10/19 08:38 | Filip Krolo v Cian Maguire | 6-2,4-6,4-6 |
| UTR Pro Zadar | 2023/10/18 07:30 | Filip Krolo v Domagoj Biljesko | 6-2,3-6,2-6 |
| UTR Pro Zadar | 2023/10/17 06:00 | Filip Krolo v Patrik Meszaros | 7-6,2-6,5-3 |
| UTR Pro Zadar | 2023/10/16 07:30 | Filip Krolo v Robert Rumler | 6-2,6-4 |