Stadium: Centre Court (2) Round: 54 Ground: Clay
| ITF M25 Padova | 2023/07/09 10:55 | Leonardo Rossi v Ryusuke Horiuchi | 6-2,6-2 |
| ITF M15 Bergamo | 2023/06/29 11:30 | Federico Iannaccone v Leonardo Rossi | 6-4,7-6 |
| ITF M15 Bergamo | 2023/06/28 07:30 | Leonardo Rossi v Luciano Carraro | 7-5,6-2 |
| ITF M15 Store | 2023/06/21 11:40 | Luca Wiedenmann v Leonardo Rossi | 7-6,6-4 |
| ITF M15 Chieti | 2023/06/14 08:00 | Leonardo Rossi v Andrea Guerrieri | 6-1,1-6,2-6 |
| ITF M15 Vaasa | 2023/06/09 11:20 | Karl Friberg v Leonardo Rossi | 6-4,6-7,7-6 |
| ITF M15 Vaasa | 2023/06/08 11:45 | Alexandros Skorilas v Leonardo Rossi | 3-6,0-6 |
| ITF M15 Vaasa | 2023/06/07 11:00 | Jonas Trinker v Leonardo Rossi | 2-6,4-6 |
| ITF M25 Padova | 2023/07/09 15:25 | Antonio Massara v Gian Marco Ortenzi | 6-3,6-7,3-10 |
| ITF M25 Biella | 2023/07/03 18:25 | Gian Marco Ortenzi v Gabriel Schenekenberg | 4-6,4-6 |
| ITF M25 Biella | 2023/07/03 07:00 | Gian Marco Ortenzi v Edoardo L Cattaneo | 6-0,6-0 |
| ITF M15 Celje | 2023/06/28 12:00 | Gian Marco Ortenzi v Jakub Katuch | 4-6,3-6 |
| ITF M15 Celje | 2023/06/27 07:00 | Gian Marco Ortenzi v Mark Wallner | 6-4,6-4 |
| ITF M15 Celje | 2023/06/26 11:25 | Gian Marco Ortenzi v Jeremy Schifris | 6-2,6-2 |
| ITF M25 Reggio Emilia | 2023/05/17 10:00 | Gian Marco Ortenzi v Kai Wehnelt | 0-6,2-6 |
| ITF M25 Reggio Emilia | 2023/05/15 15:00 | Gian Marco Ortenzi v Peter Buldorini | 6-7,4-6 |