Stadium: Court 2 Round: 27 Ground: Clay
| ITF M15 Weston | 2021/07/02 19:05 | Gerardo L Villasenor v Dane Sweeny | 6-2,6-3 |
| ITF M15 Weston | 2021/06/29 15:00 | Genaro Alberto Olivieri v Gerardo L Villasenor | 3-6,3-6 |
| ITF M25 Santo Domingo | 2021/06/10 15:50 | Gerardo L Villasenor v Conner Huertas Del Pino | 6-7,5-7 |
| ITF M25 Santo Domingo | 2021/06/09 14:45 | Yshai Oliel v Gerardo L Villasenor | 6-7,6-1,3-6 |
| ITF M25 Santo Domingo | 2021/06/01 15:55 | Gerardo L Villasenor v Diego Hidalgo | 6-4,3-6,3-6 |
| ITF M25 Pensacola | 2021/05/19 14:30 | Aidan Mchugh v Gerardo L Villasenor | 6-4,6-3 |
| ATP Acapulco | 2021/03/16 00:00 | Gerardo L Villasenor v Dominik Koepfer | 4-6,2-6 |
| Davis Cup | 2021/03/06 16:00 | Dimitar Kuzmanov v Gerardo L Villasenor | 6-7,6-4,6-7 |
| ITF M15 Weston | 2021/07/02 21:10 | Ryan Harrison v Nicolas Mejia | 6-3,6-4 |
| ITF M15 Weston | 2021/07/01 13:00 | Ryan Harrison v Tom Jomby | 6-2,6-2 |
| Challenger Orlando | 2021/06/06 14:00 | Ryan Harrison v Nick Chappell | 2-6,6-7 |
| Challenger Little Rock | 2021/05/31 21:00 | Goncalo Oliveira v Ryan Harrison | 7-5,7-6 |
| Challenger Tallahassee | 2021/04/21 19:00 | Ryan Harrison v Michael Mmoh | 4-6,3-6 |
| Challenger Tallahassee | 2021/04/20 14:00 | Ryan Harrison v Donald Young | 2-6,6-3,6-3 |
| ATP Delray Beach | 2021/01/07 19:30 | Gianluca Mager v Ryan Harrison | 3-6,6-1,6-4 |
| ATP Acapulco | 2020/02/23 01:00 | Daniel Altmaier v Ryan Harrison | 6-2,6-3 |