Stadium: Cancha 5 Round: 25 Ground: Clay
| Challenger - Barcelone | 2021/10/10 09:55 | Hugo Gaston v Dimitar Kuzmanov | 3-6,0-6 |
| Challenger - Barcelone | 2021/10/09 10:55 | Dimitar Kuzmanov v Alex Molcan | 7-5,7-6 |
| Challenger - Barcelone | 2021/10/08 09:00 | Gabashvili, Teimuraz v Dimitar Kuzmanov | 2-6,0-6 |
| Challenger - Barcelone | 2021/10/07 09:00 | Dimitar Kuzmanov v Damir Dzumhur | 6-4,6-4 |
| Challenger - Barcelone | 2021/10/05 13:10 | Dimitar Kuzmanov v Robredo, Tommy | 6-0,6-1 |
| Sofia, Bulgaria | 2021/09/29 16:55 | Kamil Majchrzak v Dimitar Kuzmanov | 7-5,6-1 |
| Sofia, Bulgaria | 2021/09/28 15:10 | Dimitar Kuzmanov v Lorenzo Musetti | 6-7,7-6,6-3 |
| Challenger Biel | 2021/09/20 12:45 | Kamke, Tobias v Dimitar Kuzmanov | 6-4,7-6 |
| Challenger Lima | 2021/10/25 16:30 | Rodriguez, Cristian v Gonzalo Villanueva | 7-6,3-6,2-6 |
| Challenger Lima | 2021/10/24 20:25 | Gonzalo Bueno v Gonzalo Villanueva | 1-6,7-6,4-6 |
| ITF M25 Lima | 2021/10/15 15:00 | Gonzalo Villanueva v Jonathan Mridha | 5-7,6-7 |
| ITF M25 Lima | 2021/10/14 19:15 | Gonzalo Villanueva v Franco Roncadelli | 6-2,6-2 |
| ITF M25 Lima | 2021/10/12 15:00 | Gonzalo Villanueva v Luca Castelnuovo | 4-6,6-4,6-4 |
| ITF M25 Lima | 2021/10/06 18:55 | Wilson Leite v Gonzalo Villanueva | 6-3,6-4 |
| Challenger Lima | 2021/09/26 18:20 | Thirouin, Jean v Gonzalo Villanueva | 6-3,1-6,6-1 |
| Ambato, Ecuador | 2021/09/19 15:00 | Gonzalo Villanueva v Luca Castelnuovo | 6-7,6-7 |