| Coupe Davis | 06/23 19:15 | 2 | Jesse Flores v Obando, Alejandro | 6-2,6-2 | |
| Coupe Davis | 06/22 20:20 | 2 | Major, Kevin v Alejandro Obando Maldonado | 6-2,6-0 | |
| Coupe Davis | 06/21 18:45 | 2 | Adolfo Daniel Vallejo v Alejandro Obando Maldonado | 6-1,6-3 | |
| Coupe Davis | 06/20 19:55 | 2 | Peter Bertran v Obando, Alejandro | 6-0,6-2 | |
| Coupe Davis | 08/06 15:50 | 2 | Patrick Sydow v Obando, Alejandro | 6-3,6-7,7-6 | |
| Coupe Davis | 08/02 14:35 | - | Obando, Alejandro v Christopher Bogelin | 6-3,6-0 | |
| Coupe Davis | 08/01 14:55 | 2 | Obando, Alejandro v Jody Maginley | 2-6,4-6 | |
| Coupe Davis | 07/02 15:40 | - | Obando, Alejandro v Ebolum Pastor Nwokolo | 6-1,6-1 | |
| Coupe Davis | 07/01 15:35 | - | Jesse Flores v Obando, Alejandro | 6-4,4-6,6-0 | |
| Coupe Davis | 06/30 16:00 | - | Obando, Alejandro v Simons, Tariq | 6-1,6-3 | |
| Coupe Davis | 06/21 15:00 | - | Obando, Alejandro v Bicknell, Jacob | 6-1,4-6,3-6 | |
| Coupe Davis | 06/20 15:00 | - | Obando, Alejandro v Gomez, Luis | 6-7,7-6,4-6 | |
| Coupe Davis | 06/19 15:00 | - | Obando, Alejandro v Mohammed, Nabeel Majeed | 6-2,6-1 | |
| Coupe Davis | 06/18 15:00 | - | Obando, Alejandro v Turino, Osviel | 6-3,6-1 | |
| Coupe Davis | 06/02 15:00 | 28 | Borba, Juan v Obando, Alejandro | 2-6,6-7 | |
| Coupe Davis | 06/01 15:00 | - | Obando, Alejandro v Bird, Dimitri | 6-2,6-1 | |
| Coupe Davis | 06/16 16:05 | 2 | Diaz, Alex v Obando, Alejandro | 6-2,6-7,6-4 | |
| Coupe Davis | 06/15 15:00 | - | Obando, Alejandro v Bicknell, Jacob | 5-7,6-1,6-4 | |
| Coupe Davis | 06/14 15:00 | 1 | Obando, Alejandro v Manders, Gavin | 6-3,6-2 | |
| Coupe Davis | 07/16 14:00 | - | Obando, Alejandro v Rivera Granja, Osmel | 3-6,4-6 | |
| Coupe Davis | 07/15 16:35 | - | Obando, Alejandro v Nunez, Pablo | 6-4,4-6,3-6 | |
| ITF Chile F5 | 04/19 17:00 | - | Obando, Alejandro v Fleming, David | 0-6,5-7 | |
| ITF Chile F5 | 04/18 17:00 | - | Obando, Alejandro v Leiva Biason, Oscar Mattias | 6-1,7-5 |