Stadium: Court 2 Round: 25 Ground: Clay
| ITF M15 Pazardzhik | 2023/05/19 10:10 | Leonardo Rossi v Simon A Ivanov | 4-6,4-6 |
| 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 Monastir | 2023/03/22 08:30 | Olaf Pieczkowski v Buvaysar Gadamauri | 2-6,6-3,2-6 |
| ITF M15 Monastir | 2023/03/19 08:30 | Olaf Pieczkowski v Lorenzo Rottoli | 6-7,3-6 |
| ITF M15 Monastir | 2023/03/18 10:15 | Simone Roncalli v Olaf Pieczkowski | 2-6,2-6 |
| ITF M15 Monastir | 2023/03/17 11:00 | Olaf Pieczkowski v Szymon Kielan | 6-1,6-1 |
| ITF M15 Monastir | 2023/03/16 08:30 | Olaf Pieczkowski v Luigi Sorrentino | 6-3,6-4 |
| ITF M15 Monastir | 2023/03/14 11:40 | Alexis Boureau v Olaf Pieczkowski | 2-6,1-6 |
| ITF M15 Monastir | 2023/03/07 10:30 | Olaf Pieczkowski v Stefano Napolitano | 4-6,3-6 |
| ITF M15 Monastir | 2023/02/12 08:30 | Ryan Nijboer v Olaf Pieczkowski | 7-6,6-2 |