Stadium: Court 09 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Castelo Branco | 2021/07/29 14:05 | Clement Chidekh v Roy Smith | 6-4,7-5 |
| ITF M15 Castelo Branco | 2021/07/28 15:30 | Ben Jones v Roy Smith | 1-6,4-6 |
| ITF M25 Idanha-A-Nova | 2021/07/22 08:00 | Gilbert S K Junior v Roy Smith | 6-3,6-2 |
| ITF M25 Idanha-A-Nova | 2021/07/14 11:05 | Roy Smith v Tiago Cacao | 5-7,6-3,6-7 |
| ITF M15 Champaign | 2021/06/23 21:50 | Roy Smith v Thomaz Bellucci | 6-7,3-6 |
| ITF M25 Santo Domingo | 2021/06/05 16:15 | Roy Smith v Aidan Mchugh | 6-3,3-6,1-6 |
| ITF M25 Santo Domingo | 2021/06/04 14:25 | Calvin Hemery v Roy Smith | 4-6,2-6 |
| ITF M25 Santo Domingo | 2021/06/03 16:45 | Roy Smith v Yshai Oliel | 4-6,6-2,6-3 |
| 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 M25 Santo Domingo | 2021/06/09 13:00 | Calvin Hemery v Jesse Flores | 7-6,7-6 |
| ITF M25 Santo Domingo | 2021/06/01 12:50 | Luis Patino v Jesse Flores | 7-5,6-3 |