Stadium: Court 10 Round: 25 Ground: Hardcourt outdoor
| ITF M25 Sintra | 2021/09/07 08:30 | Luis Patino v Jesse Flores | 2-6,6-3,5-10 |
| ITF M25 Sintra | 2021/09/06 08:30 | Hans Albert Schubert v Jesse Flores | 4-6,2-6 |
| ITF M25 Sierre | 2021/08/31 10:50 | Emiliano Maggioli v Jesse Flores | 6-1,6-0 |
| ITF M25 Decatur | 2021/08/03 15:00 | Eliot Spizzirri v Jesse Flores | 4-6,6-2,10-3 |
| ITF M25 Decatur | 2021/08/02 15:00 | Jesse Flores v Kento Takeuchi | 6-2,6-4 |
| Davis Cup | 2021/07/02 17:05 | Jesse Flores v Tariq Simons | 6-2,6-1 |
| Davis Cup | 2021/07/01 15:35 | Jesse Flores v Alejandro Obando | 6-4,4-6,6-0 |
| Davis Cup | 2021/06/30 16:30 | Jesse Flores v Nkrumah Patrick | 6-1,6-1 |
| ITF M15 Oldenzaal | 2021/08/15 14:00 | Guy Den Heijer v Paulo Knippling | 6-3,6-4 |
| ITF M15 Monastir | 2021/07/26 09:00 | Drew Baird v Paulo Knippling | 6-1,6-3 |
| ITF M15 Antalya | 2021/05/30 07:30 | Paulo Knippling v Daniil Savelev | 3-6,1-6 |
| ITF M15 Troisdorf | 2021/05/10 12:30 | Dominik Boehler v Paulo Knippling | 6-0,6-2 |
| ITF M25 Vale Do Lobo | 2021/03/07 12:00 | Paulo Knippling v Angel G Melgar | 3-6,2-6 |
| ITF M25 Vale Do Lobo | 2021/02/22 13:00 | Anthony Genov v Paulo Knippling | 6-3,6-3 |
| Challenger Sao Paulo | 2020/11/21 17:45 | Paulo Knippling v Joao Lucas Reis da Silva | 0-6,1-6 |
| ITF M25 Vale Do Lobo | 2020/10/26 10:30 | Paulo Knippling v Matheus Pucinelli De Almeida | 1-6,0-6 |