Stadium: Stadium Round: 54 Ground: Clay
| ITF M25 Vero Beach | 2021/10/18 16:00 | Matthew Dellavedova v Shane Monroe | 6-3,6-4 |
| ITF - Naples M15 | 2021/10/13 16:30 | Fletcher Scott v Matthew Dellavedova | 6-1,2-6,6-1 |
| ITF - Naples M15 | 2021/10/11 14:30 | Matthew Dellavedova v Shane Monroe | 6-2,6-2 |
| ITF - Ulcinj M15 | 2021/09/23 09:30 | Matthew Dellavedova v Juan Pablo Paz | 3-6,2-6 |
| ITF - Ulcinj M15 | 2021/09/22 11:30 | Matthew Dellavedova v Hamid Reza Nadaf | 6-4,6-3 |
| ITF - Ulcinj M15 | 2021/09/20 12:00 | Matthew Dellavedova v Daiki Yoshimura | 6-1,6-0 |
| ITF - Ulcinj M15 | 2021/09/13 08:00 | Max Houkes v Matthew Dellavedova | 6-2,6-2 |
| ITF - Ulcinj M15 | 2021/09/12 08:00 | Matthew Dellavedova v Flemming Peters | 6-3,0-6,10-6 |
| ITF M25 Vero Beach | 2021/10/18 22:00 | Juan Manuel Benitez Chavarriaga v Davide Innocenti | 6-1,6-2 |
| ITF - Naples M15 | 2021/10/15 16:10 | Blu Baker v Juan Manuel Benitez Chavarriaga | 6-7,6-2,6-0 |
| ITF - Naples M15 | 2021/10/14 15:00 | Juan Manuel Benitez Chavarriaga v Liam Draxl | 6-3,6-4 |
| ITF - Naples M15 | 2021/10/13 19:05 | Tommaso Carnevale-Miino v Juan Manuel Benitez Chavarriaga | 1-6,0-6 |
| ITF - Naples M15 | 2021/10/12 13:30 | Blu Baker v Juan Manuel Benitez Chavarriaga | 6-2,4-6,9-11 |
| ITF - Naples M15 | 2021/10/11 14:30 | Juan Manuel Benitez Chavarriaga v John Bernard | 6-3,6-4 |
| ITF M25 Vero Beach | 2019/05/01 23:35 | Juan Manuel Benitez Chavarriaga v Dmitry Popko | 2-6,5-7 |
| ITF USA F34 | 2018/11/26 16:00 | Alexis Gautier v Juan Manuel Benitez Chavarriaga | 6-1,6-4 |