Stadium: Court 1 Round: 27 Ground: Clay
| Challenger Banja Luka | 2023/08/07 09:30 | Juan Pablo Paz v Simon A Ivanov | 6-1,6-2 |
| ITF M15 Targu Jiu | 2023/08/17 12:10 | Juan Pablo Paz v Dragos N Cazacu | 6-1,7-6 |
| ITF M15 Targu Jiu | 2023/08/16 10:15 | Juan Pablo Paz v Stefan A Andreescu | 6-1,6-0 |
| Challenger Banja Luka | 2023/08/07 13:55 | Juan Pablo Paz v Aldin Setkic | 6-4,3-6,6-7 |
| Challenger Banja Luka | 2023/08/07 09:30 | Juan Pablo Paz v Simon A Ivanov | 6-1,6-2 |
| ITF M25 Pitesti | 2023/08/03 06:00 | Stefan Palosi v Juan Pablo Paz | 6-1,7-5 |
| ITF M25 Pitesti | 2023/08/02 06:00 | Felipe Derdoy v Juan Pablo Paz | 1-6,4-6 |
| ITF M25 Bacau | 2023/07/26 14:20 | Juan Pablo Paz v Dan Alexandru Tomescu | 5-7,3-6 |
| ITF M15 Uslar | 2023/07/19 14:45 | Juan Pablo Paz v Illya Beloborodko | 3-6,4-6 |
| ITF M15 Targu Jiu | 2023/08/17 07:55 | Calin Manda v Simon A Ivanov | 3-6,6-4,3-6 |
| ITF M15 Targu Jiu | 2023/08/16 07:00 | Marc Majdandzic v Simon A Ivanov | 1-6,2-6 |
| Challenger Banja Luka | 2023/08/07 09:30 | Juan Pablo Paz v Simon A Ivanov | 6-1,6-2 |
| ITF M25 Bolzano | 2023/07/31 12:50 | Simon A Ivanov v Nikolay Vylegzhanin | 4-6,0-6 |
| Challenger Verona | 2023/07/23 12:35 | Mathias Bourgue v Simon A Ivanov | 6-3,6-3 |
| ITF M15 Sofia | 2023/07/05 08:50 | Antonio Massara v Simon A Ivanov | 6-7,6-2,3-6 |
| ITF M15 Constanta | 2023/06/01 08:00 | Simon A Ivanov v Ignacio Carou | 6-4,6-2 |
| ITF M15 Constanta | 2023/05/30 11:00 | Simon A Ivanov v Kai Lemstra | 6-2,6-2 |