Stadium: Court 5 Round: 26 Ground: Hardcourt outdoor
| ITF Tunisia F5 | 2015/10/07 10:15 | Ortega-Olmedo, Roberto v Tikhomirov, Maksim | 6-3,6-1 |
| ITF M25 Monastir | 2019/10/22 11:40 | Ortega-Olmedo, Roberto v Ghorbel, Anis | 6-1,6-1 |
| Challenger Ismaning | 2019/10/14 09:20 | Lucas Miedler v Ortega-Olmedo, Roberto | 7-6,6-4 |
| Tavira, Simples M-ITF-POR-14A | 2019/10/04 09:00 | Ortega-Olmedo, Roberto v Struvay, Eduardo | 4-6,2-6 |
| Tavira, Simples M-ITF-POR-14A | 2019/10/03 09:00 | Ortega-Olmedo, Roberto v Serrano Luis, Tomas Antonio | 6-4,6-2 |
| Tavira, Simples M-ITF-POR-14A | 2019/10/02 10:00 | Ortega-Olmedo, Roberto v Cabral, Francisco | 6-4,3-6,6-4 |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 2019/09/28 12:00 | Ortega-Olmedo, Roberto v Struvay, Eduardo | 7-5,2-6,5-7 |
| Oliveira De Azemeis, Singles Q M-ITF-POR-15A | 2019/09/27 10:00 | Ortega-Olmedo, Roberto v Cacao, Tiago | 7-6,6-1 |
| 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 |
| ITF M25 Monastir | 2019/10/22 09:00 | Tikhomirov, Maksim v Petros Tsitsipas | 6-2,1-6,6-1 |
| Burgas, Singles Qualifying M-ITF-BUL-05A | 2019/10/10 07:00 | Tikhomirov, Maksim v Dimitrov, Martin | 4-6,3-6 |
| Columbus III, USA | 2019/09/17 20:55 | Escobar, Gonzalo v Tikhomirov, Maksim | 6-1,4-6,7-5 |
| Szekesfehervar, Singles Qualifying M-ITF-HUN-05A | 2019/09/03 08:00 | Genaro Alberto Olivieri v Tikhomirov, Maksim | 6-2,6-4 |
| Gyor, Qualifications Simples M-ITF-HUN-04A | 2019/08/29 08:00 | Tikhomirov, Maksim v Hampel, Lenny | 1-6,2-6 |
| Gyor, Qualifications Simples M-ITF-HUN-04A | 2019/08/28 08:00 | Tikhomirov, Maksim v Voros, Mate | 6-3,1-6,6-2 |
| ITF M25 Pitesti | 2019/08/14 06:00 | Tikhomirov, Maksim v Oleg Prihodko | 3-6,2-6 |
| Targu Mures, Singles M-ITF-ROU-05A | 2019/08/08 07:00 | Tikhomirov, Maksim v Nicholas David Ionel | 4-6,3-6 |