stadio: Court 6 Round: 24 Ground: Hardcourt outdoor
| ITF M25 Heraklion DM | 2023/11/28 13:15 | Tsitsipas/Tsitsipas v Nouchakis/Valaris | 6-3,3-6,8-10 |
| ITF M15 Heraklion DM | 2023/11/25 14:00 | Oberleitner/Schwaerzler v Tsitsipas/Tsitsipas | 7-6,6-2 |
| ITF M15 Heraklion DM | 2023/11/25 11:00 | Tsitsipas/Tsitsipas v Gea/Pietri | 6-3,6-7,10-6 |
| ITF M15 Heraklion DM | 2023/11/24 10:50 | Tsitsipas/Tsitsipas v Dragomirov/Zusman | 6-2,7-6 |
| ITF M15 Heraklion DM | 2023/11/21 12:45 | Antonopoulos/Xilas v Tsitsipas/Tsitsipas | 1-6,4-6 |
| ATP Anversa DM | 2023/10/22 12:00 | Behar/Pavlasek v Tsitsipas/Tsitsipas | 7-6,4-6,8-10 |
| ATP Anversa DM | 2023/10/21 18:25 | Tsitsipas/Tsitsipas v Arneodo/Weissborn | 4-6,7-6,13-11 |
| ATP Anversa DM | 2023/10/18 10:15 | Tsitsipas/Tsitsipas v Middelkoop/Mies | 7-5,6-3 |