Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF - M25 Santo Domingo | 2021/06/08 19:45 | Hernandez Serrano, Juan Alejandro v Rowland Phillips | 6-1,3-6,10-8 |
| ITF - M25 Santo Domingo | 2021/06/01 13:00 | Hernandez Serrano, Juan Alejandro v Hernandez Ramirez, Sergio Luis | 6-4,6-3 |
| ITF - M25 Pensacola | 2021/05/20 14:25 | Hernandez Serrano, Juan Alejandro v Gonzalez, Alejandro | 3-6,2-6 |
| ITF - M25 Pensacola | 2021/05/18 16:05 | Hernandez Serrano, Juan Alejandro v Abraham Asaba | 6-1,6-2 |
| UTR Pro Tennis Series Cancun | 2021/04/10 13:00 | Panta Herreros, Jorge Brian v Hernandez Serrano, Juan Alejandro | 6-4,5-0 |
| UTR Pro Tennis Series Cancun | 2021/04/09 15:30 | Hernandez Serrano, Juan Alejandro v Rodriguez, J. A. | 3-0 |
| UTR Pro Tennis Series Cancun | 2021/04/08 16:30 | Hernandez Serrano, Juan Alejandro v Manuel S Montemayor | 6-1,6-4 |
| UTR Pro Tennis Series Cancun | 2021/04/07 19:00 | Nathan Oppenheim v Hernandez Serrano, Juan Alejandro | 0-6,0-6 |
| ITF - M25 Santo Domingo | 2021/06/05 16:15 | Smith, Roy v Aidan Mchugh | 6-3,3-6,1-6 |
| ITF - M25 Santo Domingo | 2021/06/04 14:25 | Calvin Hemery v Smith, Roy | 4-6,2-6 |
| ITF - M25 Santo Domingo | 2021/06/03 16:45 | Smith, Roy v Yshai Oliel | 4-6,6-2,6-3 |
| ITF - M25 Santo Domingo | 2021/06/03 13:00 | Smith, Roy v Mora, Maxime | 6-0,6-0 |
| ITF - M15 Monastir | 2021/05/28 08:30 | Eliakim Coulibaly v Smith, Roy | 6-3,6-4 |
| ITF - M15 Monastir | 2021/05/27 13:15 | Arthur Bouquier v Smith, Roy | 2-6,6-7 |
| ITF - M15 Monastir | 2021/05/26 10:15 | Beale, Jeremy v Smith, Roy | 4-6,4-6 |
| ITF - M15 Monastir | 2021/05/21 08:30 | Smith, Roy v Thomas Fancutt | 0-6,4-6 |