| ITF M15 Cancun | 10/10 16:30 | 44 | Samuel Sanchez v Olaya, Jorge Alejandro | 6-4,6-1 | |
| ITF M15 Cancun | 10/03 15:30 | 44 | Pietro Mugelli v Olaya, Jorge Alejandro | 7-5,3-6,11-9 | |
| ITF M15 Cancun | 09/26 15:00 | 44 | Olaya, Jorge Alejandro v Matt Kuhar | 3-6,2-6 | |
| ITF M15 Cancun | 09/20 15:00 | 44 | Samuel Sanchez v Olaya, Jorge Alejandro | 6-3,5-7,10-4 | |
| ITF M15 Cancun | 09/19 14:00 | 44 | Embry, Patricio v Olaya, Jorge Alejandro | 1-6,6-3,8-10 | |
| ITF M15 Cancun | 09/23 14:00 | 44 | Olaya, Jorge Alejandro v Valencia, Alejandro | 6-7,2-6 | |
| ITF M15 Cancun | 09/17 15:40 | 25 | Alan Magadan v Olaya, Jorge Alejandro | 6-3,7-5 | |
| ITF M15 Cancun | 09/09 15:00 | 44 | Rousseau, Hillel v Olaya, Jorge Alejandro | 6-2,6-7,10-3 | |
| ITF M15 Cancun | 09/08 20:00 | 44 | Olaya, Jorge Alejandro v Valencia, Alejandro | Retired | |
| Challenger - Morelos | 02/18 16:00 | 166 | Manuel Guinard v Olaya, Jorge Alejandro | 6-2,6-1 | |
| ITF Mexico F3 | 05/21 14:00 | 62 | Hernandez Moreno, Omar v Olaya, Jorge Alejandro | Retired | |
| ITF Mexico F3 | 05/20 14:30 | 62 | Olaya, Jorge Alejandro v Sanchez, Erick | 6-2,6-1 | |
| ITF Mexico F2 | 05/12 15:00 | 62 | Olaya, Jorge Alejandro v Batalla Diez, Juan Ignacio | 4-6,7-6,2-6 | |
| ITF Mexico F1 | 05/06 15:00 | 62 | Rodriguez, J. A. v Olaya, Jorge Alejandro | 6-3,6-2 | |
| Challenger Morelos Qual | 02/17 18:45 | 45 | Olaya, Jorge Alejandro v Roberto Cid Subervi | 2-6,1-6 | |
| ITF Mexico F7 | 11/26 15:00 | 62 | Kalambay, Jessy v Olaya, Jorge Alejandro | 4-6,6-3,6-4 | |
| Challenger San Luis Potosi Qual | 04/08 18:00 | 45 | Mendoza, Alejandro v Olaya, Jorge Alejandro | 7-5,6-4 |