| ITF M15 Cancun | 01/30 17:15 | 26 | Dusty H. Boyer v Gerardo L Villasenor | 6-3,6-1 | |
| ITF M15 Cancun | 01/29 16:10 | 25 | Juan A H Serrano v Gerardo L Villasenor | 6-7,7-5,5-7 | |
| ITF M15 Cancun | 01/21 14:00 | 25 | Ajeet Rai v Gerardo L Villasenor | 3-6,6-2,6-2 | |
| ITF M15 Cancun | 01/15 17:20 | 25 | Gerardo L Villasenor v Brandon Walkin | Retired | |
| ITF M15 Cancun | 11/23 14:00 | 28 | Nick Chappell v Gerardo L Villasenor | 5-7,6-4,6-1 | |
| ITF M15 Cancun | 11/22 14:00 | 27 | Connor Farren v Gerardo L Villasenor | 4-6,5-7 | |
| ITF M15 Cancun | 11/21 15:35 | 26 | Eduardo Ribeiro v Gerardo L Villasenor | Retired | |
| ITF M15 Cancun | 11/20 16:45 | 25 | Ajeet Rai v Gerardo L Villasenor | 6-7,6-4,1-6 | |
| Challenger Houston | 11/12 18:00 | 24 | Alexis Galarneau v Gerardo L Villasenor | 6-3,6-3 | |
| ITF M15 Cancun | 11/08 14:00 | 27 | Joao L R Da Silva v Gerardo L Villasenor | 6-3,6-2 | |
| ITF M15 Cancun | 11/07 14:00 | 26 | Mateus Alves v Gerardo L Villasenor | 3-6,2-6 | |
| ITF M15 Cancun | 11/06 14:00 | 25 | Fernando Yamacita v Gerardo L Villasenor | 6-1,2-6,2-6 | |
| ITF M15 Cancun | 10/25 14:15 | 27 | Gerardo L Villasenor v Mwendwa Mbithi | 1-6,3-6 | |
| ITF M15 Cancun | 10/24 15:55 | 26 | Gerardo L Villasenor v Zane Khan | 7-6,0-6,6-4 | |
| ITF M15 Cancun | 10/23 20:40 | 25 | Gerardo L Villasenor v Martin Maldonado | 6-2,6-2 | |
| ITF M15 Cancun | 10/18 14:15 | 27 | Gerardo L Villasenor v Cristian Rodriguez | 6-7,5-7 | |
| ITF M15 Cancun | 10/17 16:45 | 26 | Gerardo L Villasenor v Luciano Doria | 6-3,6-3 | |
| ITF M15 Cancun | 10/15 17:30 | 25 | Gerardo L Villasenor v Jonas Maier | 6-3,6-1 | |
| ITF M15 Cancun | 10/11 14:00 | 27 | Gerardo L Villasenor v Julian Bradley | 4-6,4-6 | |
| ITF M15 Cancun | 10/10 15:35 | 26 | Gerardo L Villasenor v Ignacio Carou | 6-2,6-3 | |
| ITF M15 Cancun | 10/09 20:00 | 25 | Gerardo L Villasenor v Luciano Doria | 6-3,6-1 | |
| ITF M15 Cancun | 09/24 16:30 | 25 | Jordan Parker v Gerardo L Villasenor | Cancelled | |
| ATP Los Cabos | 07/28 01:25 | 64 | Jason Jung v Gerardo L Villasenor | 6-1,3-6,6-0 | |
| ITF M15 Cancun | 07/05 13:30 | 27 | Gerardo L Villasenor v Nicolas Moreno De Alboran | 3-6,1-6 | |
| ITF M15 Cancun | 07/04 13:30 | 26 | Gerardo L Villasenor v Alan F R Fierros | 6-3,7-6 | |
| ITF M15 Cancun | 07/03 16:10 | 25 | Gerardo L Villasenor v Jack Gibbens | 6-4,6-3 | |
| ITF M15 Cancun | 06/29 14:00 | 28 | Axel Geller v Gerardo L Villasenor | 7-5,6-1 | |
| ITF M15 Cancun | 06/28 13:30 | 27 | Nicolas Mejia v Gerardo L Villasenor | 2-6,4-6 | |
| ITF M15 Cancun | 06/27 14:45 | 26 | Mwendwa Mbithi v Gerardo L Villasenor | 4-6,2-6 | |
| ITF M15 Cancun | 06/26 13:30 | 25 | Joshua Ortlip v Gerardo L Villasenor | 4-6,3-6 |