Stadium: Court Central Round: 27 Ground: Hardcourt outdoor
| ITF Portugal F3 | 2018/03/08 13:30 | Cacao, Tiago v Ortega-Olmedo, Roberto | 6-2,1-6,6-4 |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 2019/09/26 10:00 | Ortega-Olmedo, Roberto v Perez Sanz, David | 4-6,6-0,6-1 |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 2019/09/24 16:55 | Ortega-Olmedo, Roberto v Alberto Barroso Campos | 6-2,6-2 |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 2019/09/24 12:30 | Ortega-Olmedo, Roberto v Alberto Barroso Campos | 6-2,6-2 |
| Challenger - Glasgow | 2019/09/18 14:05 | Ortega-Olmedo, Roberto v Botic Van De Zandschulp | 0-6,0-6 |
| Challenger Shanghai | 2019/09/12 02:30 | Wu, Di v Ortega-Olmedo, Roberto | 6-1,5-7,7-6 |
| Challenger Shanghai | 2019/09/10 07:25 | He, Yecong v Ortega-Olmedo, Roberto | 2-6,3-6 |
| Jinan, China | 2019/09/04 02:00 | Tung-Lin Wu v Ortega-Olmedo, Roberto | 5-7,6-2,7-5 |
| Baotou, Chine | 2019/08/29 02:00 | Frederico Ferreira Silva v Ortega-Olmedo, Roberto | 6-1,6-1 |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 2019/09/26 10:00 | Cacao, Tiago v Vivero Gonzalez, Pablo | 1-6,7-6,6-3 |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 2019/09/24 15:30 | Cacao, Tiago v Ferreira, Joao (Por) | 6-1,6-1 |
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/06 09:00 | Cacao, Tiago v Johnson, Luke | 6-4,2-6,4-6 |
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/05 10:40 | Cacao, Tiago v Salgado, Afonso | 6-2,6-1 |
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/04 11:40 | Cacao, Tiago v Coelho, Fabio | 6-4,7-5 |
| ITF M15 Sintra | 2019/08/23 11:10 | Cacao, Tiago v Mertens, Yannick | 3-6,7-6,6-7 |
| ITF M15 Sintra | 2019/08/22 09:00 | Cacao, Tiago v Brandao, Filipe | 0-6,6-3,6-4 |
| ITF M15 Sintra | 2019/08/20 13:15 | Cacao, Tiago v Pedro Araujo | 7-5,6-2 |