Stadium: Court 8 Round: 25 Ground: Clay
| ITF M15 Concepcion | 2023/12/04 14:30 | Diego F Flores v Felipe De Dios | 6-3,6-4 |
| ITF M15 Concepcion | 2023/12/03 17:30 | Diego F Flores v Benjamin Zuniga Garcia | 6-3,6-2 |
| Challenger Temuco | 2023/11/28 16:00 | Tomas Barrios Vera v Diego F Flores | 6-1,6-2 |
| ITF M25 Monastir | 2023/11/12 08:00 | Diego F Flores v Filippo Giovannini | 3-6,6-2,8-10 |
| ITF M15 Monastir | 2023/11/10 09:00 | Diego F Flores v Max Wiskandt | 7-5,5-7,3-6 |
| ITF M15 Monastir | 2023/11/09 08:30 | Sebastian Sorger v Diego F Flores | 6-7,2-6 |
| ITF M15 Monastir | 2023/11/07 08:30 | Pietro Marino v Diego F Flores | 1-6,6-7 |
| ITF M15 Monastir | 2023/11/01 08:00 | Diego F Flores v Olaf Pieczkowski | 4-6,6-2,2-6 |
| Challenger Temuco | 2023/11/26 18:40 | Benjamin Herrera v Ignacio A B Otarola | 4-6,2-6 |
| ITF M15 Monastir | 2023/05/21 08:30 | Aaron Gil Garcia v Benjamin Herrera | 6-2,6-3 |
| ITF M15 Monastir | 2023/05/14 08:30 | Derek Pham v Benjamin Herrera | 6-0,6-0 |
| ITF M15 Monastir | 2023/05/07 08:30 | Benjamin Herrera v Thomas George Brun | 2-6,5-7 |
| Challenger Concepcion | 2023/01/22 15:00 | Benjamin Herrera v Andrey Chepelev | 0-6,2-6 |
| ITF M15 Lima | 2022/11/13 16:30 | Juan M B Pazmino v Benjamin Herrera | 3-6,6-4,11-9 |
| ITF M15 Lima | 2022/11/07 17:00 | Benjamin Herrera v Nicolas Esteban Rico Arias | 2-6,6-2,12-14 |