Stadium: Court 3 Round: 25 Ground: Clay
| Challenger Trieste | 2023/07/17 10:00 | Clement Tabur v Leonardo Rossi | 7-5,6-4 |
| Challenger Trieste | 2023/07/16 11:00 | Leonardo Rossi v Mohamed Safwat | 6-4,6-2 |
| ITF M25 Padova | 2023/07/12 11:00 | Leonardo Rossi v Enrico Dalla Valle | 5-7,2-6 |
| ITF M25 Padova | 2023/07/10 12:00 | Leonardo Rossi v Gian Marco Ortenzi | 4-6,6-1,10-7 |
| 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 Vejle | 2023/07/25 07:00 | Jack Karlsson Winstrand v Gabriel Matuszewski | 6-2,6-4 |
| ITF M15 Kamen | 2023/06/26 10:00 | Jack Karlsson Winstrand v Ruben Hartig | 0-6,1-6 |
| ITF M25 Risskov/Aarhus | 2023/06/14 08:30 | Max Houkes v Jack Karlsson Winstrand | 7-5,6-2 |
| ITF M15 Vaasa | 2023/06/08 12:25 | Jack Karlsson Winstrand v Nicolas Kobelt | 2-6,6-4,3-6 |
| ITF M15 Vaasa | 2023/06/07 10:30 | Jack Karlsson Winstrand v Vesa Ahti | 4-6,6-3,6-2 |
| ITF M15 Kalmar | 2023/05/17 09:40 | Karl Friberg v Jack Karlsson Winstrand | 6-3,6-0 |
| ITF M25 Varnamo | 2023/05/10 12:10 | Jack Karlsson Winstrand v Jay Clarke | 2-6,2-6 |
| ITF M25 Varnamo | 2023/05/09 08:15 | Jack Karlsson Winstrand v Rafael Ymer | 6-2,7-5 |