Stadium: Court 3 Round: 62 Ground: Clay
| Challenger Concepcion | 2024/04/21 19:25 | Benjamin Herrera v Bautista Vilicich | 3-6,3-6 |
| ITF M15 Santiago | 2024/04/14 13:00 | Lautaro Agustin Falabella v Benjamin Herrera | 6-3,6-3 |
| ITF M15 Quillota | 2024/04/07 13:00 | Benjamin Herrera v Valentin Basel | 2-6,2-6 |
| ITF M15 Punta del Este | 2024/03/19 13:00 | Lautaro Agustin Falabella v Benjamin Herrera | 6-1,6-3 |
| ITF M15 Punta del Este | 2024/03/18 13:00 | Benjamin Herrera v Benjamin Denis Alarcon | 6-4,6-1 |
| ITF M15 Punta del Este | 2024/03/17 12:00 | Rocco Mariani v Benjamin Herrera | 5-7,7-5,2-10 |
| ITF M15 Punta del Este | 2024/03/10 17:00 | Benjamin Herrera v Tobia Grandinetti | 2-6,6-4,6-10 |
| ITF M15 Concepcion | 2023/12/12 17:45 | Benjamin Herrera v Miguel Angel Cabrera | 2-6,4-6 |
| ITF M25 Pazardzhik | 2023/10/05 10:25 | Damien Wenger v Plamen Milushev | 6-2,6-1 |
| ITF M25 Pazardzhik | 2023/10/04 10:15 | Jasza Szajrych v Plamen Milushev | 6-3,6-7,5-7 |
| ITF M25 Pazardzhik | 2023/10/02 13:15 | Plamen Milushev v Maxwell Benson | 6-4,7-5 |
| ITF M25 Pazardzhik | 2023/10/02 07:30 | Razvan Baiant v Plamen Milushev | 4-6,6-4,5-10 |
| ITF M25 Pazardzhik | 2023/09/27 10:55 | Hynek Barton v Plamen Milushev | 6-3,6-3 |
| ITF M25 Pazardzhik | 2023/09/25 12:00 | Plamen Milushev v Andrea Meduri | 1-6,7-6,10-7 |
| ITF M25 Pazardzhik | 2023/09/24 07:00 | Razvan Baiant v Plamen Milushev | 6-4,1-6,3-10 |
| ITF M15 Sofia | 2023/07/02 06:30 | Plamen Milushev v Pierre Yves Bailly | 6-7,2-6 |