Estadio: Court 5 Round: 54 Ground: Hardcourt indoor
| ITF M25 Weston | 2022/01/23 17:00 | Corey Craig v Nathan Taschereau | 6-3,6-0 |
| ITF M15 Heraklion | 2023/11/22 13:05 | Jannik Maute v Simon Freund | 6-3,6-3 |
| ITF M15 Heraklion | 2023/11/21 07:00 | Lars Goran Verwerft v Simon Freund | 6-1,5-7,8-10 |
| ITF M15 Heraklion | 2023/11/20 13:45 | Adrian Arcon v Simon Freund | 2-6,0-6 |
| ITF M15 Heraklion | 2023/11/19 15:30 | Vincent Jonah Strauch v Simon Freund | 3-6,3-6 |
| ITF M25 Heraklion | 2023/11/14 07:30 | James Davis v Simon Freund | 6-4,5-7,10-7 |
| ITF M25 Heraklion | 2023/11/13 08:30 | Graham Maassen v Simon Freund | 3-6,2-6 |
| ITF M25 Heraklion | 2023/11/07 07:30 | Guy Den Heijer v Simon Freund | 6-2,3-6,10-5 |
| ITF M25 Heraklion | 2023/11/06 07:00 | Graham Maassen v Simon Freund | 4-6,2-6 |