Stadium: Court 7 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Cancun | 2019/11/20 16:45 | Ajeet Rai v Gerardo L Villasenor | 6-7,6-4,1-6 |
| ATP Auckland | 2020/01/11 00:10 | Thiago Monteiro v Ajeet Rai | 6-4,6-2 |
| ITF M15 Te Anau | 2020/01/02 21:00 | Ajeet Rai v Andrea Vavassori | 2-6,5-7 |
| ITF M15 Te Anau | 2020/01/01 22:15 | Lorenzo Musetti v Ajeet Rai | 1-6,6-3,6-7 |
| ITF M15 Te Anau | 2019/12/30 23:00 | Ajeet Rai v William Hatzis | 6-3,6-2 |
| ITF M15 Cancun | 2019/11/20 16:45 | Ajeet Rai v Gerardo L Villasenor | 6-7,6-4,1-6 |
| ITF M15 Cancun | 2019/11/19 14:00 | Cameron Green v Ajeet Rai | 3-6,3-6 |
| ITF M15 Cancun | 2019/11/17 15:30 | Felipe M Sarrasague v Ajeet Rai | 5-7,6-7 |
| ITF M15 Cancun | 2019/11/13 14:00 | Jorge Panta v Ajeet Rai | 6-4,6-4 |
| ITF M15 Cancun | 2019/11/23 14:00 | Nick Chappell v Gerardo L Villasenor | 5-7,6-4,6-1 |
| ITF M15 Cancun | 2019/11/22 14:00 | Connor Farren v Gerardo L Villasenor | 4-6,5-7 |
| ITF M15 Cancun | 2019/11/20 16:45 | Ajeet Rai v Gerardo L Villasenor | 6-7,6-4,1-6 |
| Challenger Houston | 2019/11/12 18:00 | Alexis Galarneau v Gerardo L Villasenor | 6-3,6-3 |
| ITF M15 Cancun | 2019/11/08 14:00 | Joao Lucas Reis da Silva v Gerardo L Villasenor | 6-3,6-2 |
| ITF M15 Cancun | 2019/11/07 14:00 | Mateus Alves v Gerardo L Villasenor | 3-6,2-6 |
| ITF M15 Cancun | 2019/11/06 14:00 | Fernando Yamacita v Gerardo L Villasenor | 6-1,2-6,2-6 |
| ITF M15 Cancun | 2019/10/25 14:15 | Gerardo L Villasenor v Mwendwa Mbithi | 1-6,3-6 |