| ITF M25 Monastir | 10/26 09:00 | 28 | Ortega-Olmedo, Roberto v Petros Chrysochos | 3-6,1-6 | |
| ITF M25 Monastir | 10/25 09:00 | 27 | [246] Ortega-Olmedo, Roberto v Bergevi, Filip [474] | 6-3,6-3 | |
| ITF M25 Monastir | 10/24 10:50 | 26 | Ortega-Olmedo, Roberto v Tikhomirov, Maksim | 6-2,6-4 | |
| ITF M25 Monastir | 10/22 11:40 | 25 | [246] Ortega-Olmedo, Roberto v Ghorbel, Anis [476] | 6-1,6-1 | |
| Challenger Ismaning | 10/14 09:20 | 24 | Lucas Miedler v Ortega-Olmedo, Roberto | 7-6,6-4 | |
| Tavira, Simples M-ITF-POR-14A | 10/04 09:00 | 27 | [248] Ortega-Olmedo, Roberto v Struvay, Eduardo [441] | 4-6,2-6 | |
| Tavira, Simples M-ITF-POR-14A | 10/03 09:00 | 26 | Ortega-Olmedo, Roberto v Serrano Luis, Tomas Antonio | 6-4,6-2 | |
| Tavira, Simples M-ITF-POR-14A | 10/02 10:00 | 25 | [248] Ortega-Olmedo, Roberto v Cabral, Francisco [427] | 6-4,3-6,6-4 | |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 09/28 12:00 | 28 | [245] Ortega-Olmedo, Roberto v Struvay, Eduardo [439] | 7-5,2-6,5-7 | |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 09/27 10:00 | 27 | Ortega-Olmedo, Roberto v Cacao, Tiago | 7-6,6-1 | |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 09/26 10:00 | 26 | [245] Ortega-Olmedo, Roberto v Perez Sanz, David [473] | 4-6,6-0,6-1 | |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 09/24 16:55 | 25 | Ortega-Olmedo, Roberto v Alberto Barroso Campos | 6-2,6-2 | |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 09/24 12:30 | - | Ortega-Olmedo, Roberto v Alberto Barroso Campos | 6-2,6-2 | |
| Challenger - Glasgow | 09/18 14:05 | 25 | [241] Ortega-Olmedo, Roberto v Botic Van De Zandschulp [287] | 0-6,0-6 | |
| Challenger Shanghai | 09/12 02:30 | 26 | [438] Wu, Di v Ortega-Olmedo, Roberto [243] | 6-1,5-7,7-6 | |
| Challenger Shanghai | 09/10 07:25 | 25 | He, Yecong v Ortega-Olmedo, Roberto | 2-6,3-6 | |
| Jinan, China | 09/04 02:00 | 25 | [269] Tung-Lin Wu v Ortega-Olmedo, Roberto [242] | 5-7,6-2,7-5 | |
| Baotou, Chine | 08/29 02:00 | 26 | [282] Frederico Ferreira Silva v Ortega-Olmedo, Roberto [242] | 6-1,6-1 | |
| Baotou, Chine | 08/28 02:00 | 25 | [409] Hamou, Maxime v Ortega-Olmedo, Roberto [242] | 6-7,6-7 | |
| Challenger Meerbusch | 08/16 12:30 | 27 | [254] Ortega-Olmedo, Roberto v Krstin, Pedja [239] | 0-6,2-6 | |
| Challenger Meerbusch | 08/15 10:30 | 26 | [254] Ortega-Olmedo, Roberto v Raul Brancaccio [277] | 6-4,6-7,6-4 | |
| Challenger Meerbusch | 08/14 09:20 | 25 | [254] Ortega-Olmedo, Roberto v Pavlasek, Adam [382] | 6-3,6-4 | |
| Pozoblanco, Singles Qualifying M-ITF-ESP-24A | 08/08 18:00 | 26 | Ortega-Olmedo, Roberto v Lescure, Mick | 6-4,3-6,4-6 | |
| Pozoblanco, Singles Qualifying M-ITF-ESP-24A | 08/07 18:10 | 25 | [259] Ortega-Olmedo, Roberto v Dubrivnyy, Artem [488] | 6-4,6-4 | |
| Segovia, Spain | 08/01 10:00 | 26 | [450] Eriksson, Markus v Ortega-Olmedo, Roberto [271] | 1-6,6-1,7-5 | |
| Segovia, Spain | 07/31 10:35 | 25 | [413] Ocleppo, Julian v Ortega-Olmedo, Roberto [271] | 7-6,3-6,4-6 | |
| Binghamton, USA | 07/24 19:20 | 25 | [241] Sugita, Yuichi v Ortega-Olmedo, Roberto [274] | 7-5,6-1 | |
| Binghamton, USA | 07/23 20:45 | 24 | [274] Ortega-Olmedo, Roberto v Stefan Kozlov [402] | Retired | |
| Gatineau, Canada | 07/15 21:30 | 24 | [278] Ortega-Olmedo, Roberto v Skander Mansouri [446] | 1-6,4-6 | |
| Challenger Winnipeg | 07/11 20:00 | 26 | [272] Cem Ilkel v Ortega-Olmedo, Roberto [282] | 7-6,6-3 |