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