Stadium: Cancha 3 Round: 14 Ground: Clay
| ITF - M25 Ithaca | 2024/01/16 17:40 | Preston Stearns v Simon Freund | 7-6,6-3 |
| ITF - M25 Ithaca | 2024/01/15 17:30 | Nathan Taschereau v Simon Freund | 0-6,1-6 |
| 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 |
| Challenger - Santiago | 2024/03/10 17:25 | Orlando Luz v Conner Huertas Del Pino | 6-2,6-4 |
| Challenger - Santa Cruz | 2024/03/03 18:55 | Federico Zeballos v Conner Huertas Del Pino | 6-1,6-2 |
| Challenger - Temuco | 2023/11/30 16:15 | Alafia Ayeni v Conner Huertas Del Pino | 3-6,6-0,6-3 |
| Challenger - Temuco | 2023/11/28 13:00 | Andres Andrade v Conner Huertas Del Pino | 6-3,5-7,2-6 |
| Challenger - Temuco | 2023/11/27 13:00 | Gabriel Decamps v Conner Huertas Del Pino | 6-0,6-2 |
| Challenger - Temuco | 2023/11/26 13:00 | Gabriel Roveri Sidney v Conner Huertas Del Pino | 1-6,1-6 |
| Challenger - Brasilia | 2023/11/19 15:20 | Mateus Alves v Conner Huertas Del Pino | 6-4,7-6 |
| Challenger - Lima | 2023/11/09 18:05 | Alejandro Tabilo v Conner Huertas Del Pino | 6-3,6-4 |