Round: 54 Ground: Clay
| ITF Dominican Republic F2 | 2018/12/04 14:00 | Montero, Jorge v Fermin Tenti | 2-6,7-5,2-6 |
| ITF Chile F3 | 2018/11/28 14:00 | Montero, Jorge v Pena Lopez, Manuel | 4-6,0-6 |
| ITF Chile F3 | 2018/11/26 17:35 | Nicolas Bruna v Montero, Jorge | 4-6,4-6 |
| ITF Chile F2 | 2018/11/21 16:00 | Montero, Jorge v Zukas, Matias | 1-6,1-6 |
| ITF Chile F2 | 2018/11/19 16:30 | Castro, Cristobal v Montero, Jorge | 4-6,2-6 |
| ITF Chile F1 | 2018/11/14 19:35 | Montero, Jorge v Martinez, Mirko | 4-6,6-7 |
| Challenger Campinas | 2018/09/30 15:30 | Montero, Jorge v Miele, Andre | 4-6,6-3,3-6 |
| ITF Spain F28 | 2018/09/18 11:00 | Montero, Jorge v Pol Martin Tiffon | 3-6,6-3,2-6 |
| USA F33, Singles | 2018/11/17 15:00 | Boris Butulija v Cash, Robert | 7-5,6-1 |
| ITF USA F18 | 2018/06/25 14:00 | Cash, Robert v Fifea, Catalin | 3-6,4-6 |
| ITF USA F38 | 2017/11/18 15:00 | Alexander Brown v Cash, Robert | 3-6,6-2,6-1 |