Estádio: Court 3 Round: 26 Ground: Clay
| ITF - M15 Pazardzhik | 2023/05/18 10:20 | Viktor Markov v Leonardo Rossi | 6-7,7-5,6-7 |
| ITF - M25 Santa Margherita | 2023/04/17 13:50 | Leonardo Rossi v Julian Ocleppo | 2-6,3-6 |
| ITF - M25 Santa Margherita | 2023/04/10 08:30 | Leonardo Rossi v Mateo Nicolas Martinez | 4-6,7-5,8-10 |
| ITF - M25 Santa Margherita | 2023/04/09 08:30 | Leonardo Rossi v Gregoire Gervail | 6-1,6-4 |
| ITF - M25 Trento | 2023/03/28 13:15 | Jerome Kym v Leonardo Rossi | 7-5,3-6,6-2 |
| ITF - M15 Heraklion | 2023/03/23 08:00 | Leonardo Rossi v Andrea Picchione | 5-7,2-6 |
| ITF - M15 Heraklion | 2023/03/21 08:00 | Leonardo Rossi v Gabriele Maria Noce | 6-2,7-6 |
| ITF - M15 Heraklion | 2023/03/15 09:20 | Simon Carr v Leonardo Rossi | 6-4,7-6 |
| ITF - M15 Pazardzhik | 2023/05/18 10:30 | Lorenzo Vatteroni v Simon A Ivanov | 2-6,2-6 |
| ITF - M15 Alaminos-Larnaca | 2023/05/04 07:30 | Dragos N Cazacu v Simon A Ivanov | 1-6,6-1,6-2 |
| ITF - M15 Alaminos-Larnaca | 2023/05/02 08:50 | Simon A Ivanov v Photos Photiades | 6-4,6-0 |
| ITF - M15 Alaminos-Larnaca | 2023/04/30 08:00 | Simon A Ivanov v Guy Den Ouden | 7-6,2-6,4-6 |
| ITF - M15 Alaminos-Larnaca | 2023/04/29 08:00 | Sergey Fomin v Simon A Ivanov | 1-6,7-6,3-6 |
| ITF - M15 Alaminos-Larnaca | 2023/04/28 07:00 | Elmer Moller v Simon A Ivanov | 5-7,6-4,6-7 |
| ITF - M15 Alaminos-Larnaca | 2023/04/27 09:25 | Dragos N Cazacu v Simon A Ivanov | 2-6,2-6 |
| ITF - M15 Alaminos-Larnaca | 2023/04/26 08:50 | Alexandros Skorilas v Simon A Ivanov | 6-2,4-6,1-6 |