| ITF - Katar F4 | 12/08 12:00 | 28 | [352] Maxime Hamou v Roberto O-Olmedo [311] | 1-6,6-7 | |
| ITF - Katar F4 | 12/07 14:40 | 27 | [380] Maximilian Neuchrist v Roberto O-Olmedo [311] | 6-2,4-6,2-6 | |
| ITF - Katar F4 | 12/06 14:40 | 26 | Jaimee Floyd Angele v Roberto O-Olmedo | 3-6,2-6 | |
| ITF - Katar F4 | 12/05 19:00 | 25 | Ryan Peniston v Roberto Ortega-Olmedo | 1-6,2-6 | |
| ITF - Katar F4 | 12/05 16:30 | - | Ryan Peniston v Roberto O-Olmedo | 1-6,2-5 | |
| ITF - Ägypten F34 | 11/16 13:30 | 26 | Roman Safiullin v Roberto Ortega-Olmedo | 7-6,7-6 | |
| ITF - Ägypten F34 | 11/15 17:10 | 25 | [408] Oleg Prihodko v Roberto Ortega-Olmedo [291] | 3-6,2-6 | |
| ITF - Ägypten F33 | 11/10 13:30 | 27 | Roman Safiullin v Roberto Ortega-Olmedo | 6-2,6-7,6-4 | |
| ITF - Ägypten F33 | 11/09 13:30 | 26 | Olexiy Kolisnyk v Roberto Ortega-Olmedo | 5-7,0-6 | |
| ITF - Ägypten F33 | 11/08 16:50 | 25 | Olly Sadler v Roberto Ortega-Olmedo | 3-6,2-6 | |
| Challenger - Las Vegas | 10/17 20:40 | 25 | [288] Roberto Ortega-Olmedo v Cameron Norrie [110] | 4-6,3-6 | |
| Challenger - Fairfield - Qualifikation | 10/07 20:55 | 45 | Roberto O-Olmedo v Alexander Ward | 1-6,1-6 | |
| Challenger - Monterrey | 10/03 21:45 | 25 | [277] Roberto Ortega-Olmedo v Austin Krajicek [268] | 4-6,5-7 | |
| ITF - Portugal F20 | 09/28 09:30 | 27 | [287] Sadio Doumbia v Roberto Ortega-Olmedo [282] | 6-1,1-6,6-3 | |
| ITF - Portugal F20 | 09/27 09:30 | 26 | Miguel Semedo v Roberto Ortega-Olmedo | 0-6,2-6 | |
| ITF - Portugal F20 | 09/26 11:05 | 25 | [467] Fred Gil v Roberto Ortega-Olmedo [282] | 5-7,7-5,6-7 | |
| ATP - Metz - Qualifikation | 09/17 08:00 | 45 | [120] Stefanos Tsitsipas v Roberto Ortega-Olmedo [282] | 6-2,7-5 | |
| Challenger - Istanbul | 09/11 09:00 | 25 | Roberto O-Olmedo v Karim-Mohamed Maamoun | 4-6,3-6 | |
| Challenger - Portoroz | 08/09 13:00 | 26 | [296] Roberto Ortega-Olmedo v Pedro Martinez [313] | 6-4,0-6,3-6 | |
| Challenger - Portoroz | 08/08 16:45 | 25 | [473] Ljubomir Celebic v Roberto Ortega-Olmedo [296] | 3-6,3-6 | |
| Challenger - Segovia - Qualifikation | 07/31 10:00 | 54 | Roberto Ortega-Olmedo v David Vega Hernandez | 3-6,0-6 | |
| Challenger - Segovia - Qualifikation | 07/30 09:00 | 46 | Roberto O-Olmedo v Ricardo Villacorta-Alonso | Retired | |
| Challenger - Astana | 07/20 05:00 | 26 | [295] Roberto Ortega-Olmedo v Aldin Setkic [210] | 2-6,6-7 | |
| Challenger - Astana | 07/19 05:00 | 25 | [423] Evgeny Karlovskiy v Roberto Ortega-Olmedo [295] | 3-6,5-7 | |
| ITF - Portugal F11 | 07/15 11:00 | 28 | [244] Alex De Minaur v Roberto O.-Olmedo [360] | 6-1,6-3 | |
| ITF - Portugal F11 | 07/14 11:00 | 27 | Roberto O.-Olmedo v Antoine Escoffier | 7-6,6-3 | |
| ITF - Portugal F11 | 07/12 11:40 | 26 | Roberto O.-Olmedo v Romain Bauvy | 6-0,6-1 | |
| ITF - Portugal F11 | 07/11 09:30 | 25 | Roberto O.-Olmedo v Jorge H-Ruano | 4-6,6-3,6-3 | |
| ITF - Portugal F10 | 07/09 11:00 | 29 | [360] Roberto Ortega-Olmedo v Frederico Ferreira Silva [343] | 6-3,6-2 | |
| ITF - Portugal F10 | 07/08 11:00 | 28 | [284] Albano Olivetti v Roberto Ortega-Olmedo [360] | 2-6,7-6,2-6 |