Stadium: Stadium Court Round: 26 Ground: Hardcourt outdoor
| Challenger Palmas del Mar | 2023/06/13 23:10 | Gustavo Heide v Tristan Schoolkate | 7-6,6-3 |
| Challenger Palmas del Mar | 2023/06/12 15:00 | Marius Copil v Gustavo Heide | 3-6,4-6 |
| Challenger Palmas del Mar | 2023/06/11 17:15 | Ji Sung Nam v Gustavo Heide | 4-6,4-6 |
| Challenger Tyler | 2023/06/06 16:35 | Gustavo Heide v Alexis Galarneau | 4-6,2-6 |
| Challenger Tyler | 2023/06/05 19:50 | Gustavo Heide v Ernesto Escobedo | 7-5,3-6,7-6 |
| Challenger Tyler | 2023/06/04 21:00 | Maks Kasnikowski v Gustavo Heide | 6-7,3-6 |
| Challenger Little Rock | 2023/05/28 17:00 | Christian Langmo v Gustavo Heide | 6-2,4-6,6-3 |
| Challenger Coquimbo | 2023/05/03 14:00 | Gustavo Heide v Facundo Juarez | 5-7,3-6 |
| Challenger Palmas del Mar | 2023/06/13 22:25 | Alex Rybakov v Nicolas Moreno De Alboran | 7-6,6-3 |
| Challenger Palmas del Mar | 2023/06/12 17:40 | Evan Zhu v Alex Rybakov | 7-6,4-6,6-3 |
| Challenger Palmas del Mar | 2023/06/11 17:05 | Alfredo Perez v Alex Rybakov | 7-5,1-6,2-6 |
| ITF M25 Most | 2023/05/24 10:45 | Hynek Barton v Alex Rybakov | 6-3,6-3 |
| ITF M25 Prague | 2023/05/17 09:25 | Petr Nouza v Alex Rybakov | 6-4,6-3 |
| Challenger Prague | 2023/05/08 09:00 | Guido Andreozzi v Alex Rybakov | 6-3,6-3 |
| Challenger Prague Qual | 2023/05/07 09:50 | Patrik Rikl v Alex Rybakov | 6-7,5-7 |
| ITF M25 Sabadell | 2023/05/03 11:45 | Alex Rybakov v David Jorda Sanchis | 6-7,3-6 |