| Challenger - Koblenz | 01/20 13:00 | 29 | [275] Gianluca Mager v Ortega-Olmedo, Roberto [323] | 2-6,7-6,6-2 | |
| Challenger - Koblenz | 01/19 16:00 | 28 | [345] Pavel Kotov v Ortega-Olmedo, Roberto [323] | 5-7,6-3,3-6 | |
| Challenger - Koblenz | 01/18 17:25 | 27 | [195] Ymer, Mikael v Ortega-Olmedo, Roberto [323] | 7-6,1-6,3-6 | |
| Challenger - Koblenz | 01/17 18:15 | 26 | [323] Ortega-Olmedo, Roberto v Maden, Yannick [124] | 6-4,3-6,6-3 | |
| Challenger - Koblenz | 01/15 18:50 | 25 | [219] Zdenek Kolar v Ortega-Olmedo, Roberto [323] | 2-6,4-6 | |
| Challenger - Koblenz | 01/14 18:20 | 24 | [417] Marek Gengel v Ortega-Olmedo, Roberto [323] | 6-7,3-6 | |
| Challenger Columbus | 01/08 22:15 | 25 | [247] Norbert Gombos v Ortega-Olmedo, Roberto [318] | 6-4,5-7,7-6 | |
| Challenger Columbus | 01/07 23:10 | 24 | Ortega-Olmedo, Roberto v Mcnally, John | 6-2,6-2 | |
| Orlando, USA | 12/31 15:00 | 166 | [319] Ortega-Olmedo, Roberto v Joao Menezes [398] | 6-4,3-6,5-7 | |
| USA F33, Singles | 11/24 15:00 | 29 | Findel-Hawkins, Jack v Ortega-Olmedo, Roberto | 6-3,2-6,2-6 | |
| USA F33, Singles | 11/23 17:30 | 28 | [297] Maxime Cressy v Ortega-Olmedo, Roberto [305] | 6-7,6-7 | |
| USA F33, Singles | 11/22 17:15 | 27 | Brooksby, Jenson v Ortega-Olmedo, Roberto | Retired | |
| USA F33, Singles | 11/21 17:00 | 26 | Mcnally, John v Ortega-Olmedo, Roberto | 1-6,2-6 | |
| USA F33, Singles | 11/20 21:45 | 25 | Dunbar, Jacob v Ortega-Olmedo, Roberto | 2-6,2-6 | |
| Houston, USA | 11/15 16:00 | 26 | [221] Kamil Majchrzak v Ortega-Olmedo, Roberto [311] | 6-3,4-6,6-3 | |
| Houston, USA | 11/13 22:55 | 25 | Sumit Sarkar v Ortega-Olmedo, Roberto | 6-7,1-6 | |
| Challenger Las Vegas | 10/25 19:20 | 26 | [315] Ortega-Olmedo, Roberto v Jason Jung [127] | 4-6,4-6 | |
| Challenger Las Vegas | 10/23 22:45 | 25 | [271] Jan Choinski v Ortega-Olmedo, Roberto [315] | 3-6,4-6 | |
| Challenger Las Vegas | 10/22 18:00 | 54 | [379] Hugo Grenier v Ortega-Olmedo, Roberto [315] | 7-6,3-6,4-6 | |
| Challenger Las Vegas | 10/21 19:20 | 46 | Alex Rybakov v Ortega-Olmedo, Roberto | 6-7,4-6 | |
| Challenger Las Vegas | 10/20 20:00 | 45 | Gomez, Lucas v Ortega-Olmedo, Roberto | 2-6,7-5,0-6 | |
| Challenger Calgary | 10/15 20:05 | 25 | [325] Enzo Couacaud v Ortega-Olmedo, Roberto [316] | 6-2,4-6,6-3 | |
| Challenger Fairfield | 10/06 22:15 | 45 | [69] Nielsen, Frederik v Ortega-Olmedo, Roberto [316] | 6-2,6-2 | |
| Challenger Stockton | 09/29 17:00 | 45 | [327] Ortega-Olmedo, Roberto v Marcos Giron [356] | 4-6,4-6 | |
| Challenger Tiburon | 09/25 21:55 | 25 | [234] Ernesto Escobedo v Ortega-Olmedo, Roberto [327] | 6-1,7-6 | |
| Challenger Tiburon | 09/24 17:00 | 54 | [259] Jan Choinski v Ortega-Olmedo, Roberto [327] | 6-7,3-6 | |
| Challenger Tiburon | 09/23 17:00 | 46 | [351] Marcos Giron v Ortega-Olmedo, Roberto [325] | 3-6,6-1,5-7 | |
| Challenger Tiburon | 09/22 17:00 | 45 | [416] Sebastian Fanselow v Ortega-Olmedo, Roberto [325] | 1-6,2-6 | |
| Challenger Columbus | 09/17 16:35 | 25 | [193] Alexei Popyrin v Ortega-Olmedo, Roberto [325] | 4-6,7-6,7-5 | |
| Challenger Cary | 09/11 21:10 | 25 | [321] Ortega-Olmedo, Roberto v Dominik Koepfer [188] | 6-3,5-7,1-6 |