Stadium: Court 2 Round: 44
| ITF M25 Portoviejo | 2021/07/26 14:30 | Mateo Barreiros Reyes v Kessler, Mcclain | 6-1,6-1 |
| ITF M25 Portoviejo | 2021/07/28 16:00 | Mateo Barreiros Reyes v Gonzalo Lama | 3-6,4-6 |
| ITF M25 Portoviejo | 2021/07/26 20:10 | Gomez, Mateo v Mateo Barreiros Reyes | 6-7,6-7 |
| ITF M25 Portoviejo | 2021/07/26 14:30 | Mateo Barreiros Reyes v Kessler, Mcclain | 6-1,6-1 |
| ITF - M25 Santo Domingo | 2021/06/06 15:00 | Jachuck, Ronan v Mateo Barreiros Reyes | 6-4,6-1 |
| ITF - M25 Santo Domingo | 2021/05/30 15:30 | Mateo Barreiros Reyes v Jesse Flores | 2-6,4-6 |
| ITF - M15 Monastir | 2021/03/29 08:00 | Mateo Barreiros Reyes v Fausto Tabacco | 3-6,3-6 |
| ITF - M15 Monastir | 2021/03/28 10:30 | O'Neill, Daniel v Mateo Barreiros Reyes | 3-6,3-6 |
| ITF - M15 Monastir | 2021/03/22 12:30 | Ribeiro Marcondes, Igor v Mateo Barreiros Reyes | 6-4,6-4 |
| ITF M25 Guayaquil | 2021/08/01 16:30 | Juan Sebastian Osorio v Kessler, Mcclain | 1-6,3-6 |
| ITF M25 Portoviejo | 2021/07/26 14:30 | Mateo Barreiros Reyes v Kessler, Mcclain | 6-1,6-1 |
| UTR Pro Tennis Series Atlanta | 2021/07/16 15:54 | Kessler, Mcclain v Phillip Jordan | 4-6,4-6 |
| UTR Pro Tennis Series Atlanta | 2021/07/15 16:30 | Kessler, Mcclain v Thomson, Connor | 6-3,2-1 |
| UTR Pro Tennis Series Atlanta | 2021/07/13 21:00 | Kessler, Mcclain v Ravichander, Ishaan | 6-7,4-6 |
| UTR Pro Tennis Series Atlanta | 2021/07/12 13:30 | Kessler, Mcclain v Rehman, Huzaifa A. | 6-4,5-3 |
| UTR Pro Tennis Series Atlanta | 2021/04/18 12:30 | Kessler, Mcclain v Daniel Milavsky | 6-3,4-6,4-6 |
| UTR Pro Tennis Series Atlanta | 2021/04/17 12:30 | Kessler, Mcclain v Jonny Ho | 6-2,6-6 |