Stadium: Court 7 Round: 25 Ground: Hardcourt outdoor
| ITF M25 Naples | 2019/10/30 14:00 | Alan Kohen v Maximiliano Estevez | 6-3,4-6,6-0 |
| ITF M15 Cancun | 2019/10/26 14:15 | Maximiliano Estevez v Mwendwa Mbithi | 6-0,6-2 |
| ITF M15 Cancun | 2019/10/25 14:15 | Maximiliano Estevez v Juan Sebastian Gomez | 6-3,6-3 |
| ITF M15 Cancun | 2019/10/24 16:45 | Maximiliano Estevez v Jonas Maier | 6-3,6-1 |
| ITF M15 Cancun | 2019/10/22 16:30 | Maximiliano Estevez v David Volfson | 6-1,7-6 |
| ITF M15 Cancun | 2019/10/17 14:00 | Maximiliano Estevez v Sergio Luis H Ramirez | 6-1,5-7,3-6 |
| ITF M15 Cancun | 2019/10/15 14:00 | Maximiliano Estevez v Ignacio Carou | 6-1,6-2 |
| ITF M15 Cancun | 2019/10/11 14:00 | Maximiliano Estevez v Jorge Panta | 3-6,6-2,2-6 |
| ITF M15 Cancun | 2020/01/13 14:00 | Fletcher Scott v Jason Kros | 2-6,6-3,5-10 |
| ITF M15 Cancun | 2020/01/12 17:00 | Adrian Chamdani v Jason Kros | 2-6,0-6 |
| ITF M15 Tallahassee | 2019/12/05 15:00 | Strong Kirchheimer v Jason Kros | 6-3,7-5 |
| ITF M15 Tallahassee | 2019/12/04 20:55 | Alex Knaff v Jason Kros | 6-1,3-6,6-7 |
| ITF M15 Tallahassee | 2019/12/02 15:00 | Jason Kros v Victor Castro | 6-3,6-1 |
| ITF M25 Naples | 2019/11/18 14:00 | Alvaro Fernandez Horta v Jason Kros | 4-6,6-4,10-6 |
| ITF M25 Naples | 2019/11/17 14:00 | Sebastian Murillo v Jason Kros | 1-6,4-6 |
| ITF M25 Orlando | 2019/11/11 15:00 | Jose Pereira v Jason Kros | 6-3,7-6 |