Stadium: Court 2 Round: 54 Ground: Hardcourt outdoor
| ITF M25 Dharwad | 2023/10/15 06:30 | Jack Karlsson Winstrand v Dheeraj Kodancha Srinivasan | 6-2,6-3 |
| ITF M15 Ahmedabad | 2023/10/09 04:30 | Jack Karlsson Winstrand v Shivank Bhatnagar | 4-6,7-6,8-10 |
| ITF M15 Ahmedabad | 2023/10/08 04:30 | Jack Karlsson Winstrand v Tarun Karra | 7-5,7-5 |
| ITF M25 Falun | 2023/09/26 13:55 | Jack Karlsson Winstrand v Karl Friberg | 3-6,6-7 |
| ITF M25 Falun | 2023/09/25 08:00 | Adam Heinonen v Jack Karlsson Winstrand | 6-1,6-3 |
| ITF M25 Falun | 2023/09/24 08:00 | Samuel Rovai v Jack Karlsson Winstrand | 6-7,2-6 |
| ITF M15 Danderyd | 2023/09/20 10:30 | Milos Karol v Jack Karlsson Winstrand | 2-6,6-3,6-4 |
| ITF M15 Danderyd | 2023/09/19 08:00 | Jack Karlsson Winstrand v Julien De Cuyper | 6-4,6-1 |
| ITF M25 Dharwad | 2023/10/15 06:30 | Jake Bhangdia v Enrico Giacomini | 1-6,3-6 |
| ITF M25 Pozzuoli | 2023/09/10 19:40 | Andrea Colombo v Enrico Giacomini | 7-5,6-4 |
| ITF M25 Maribor | 2023/09/05 07:50 | Tim Heger v Enrico Giacomini | 6-3,6-2 |
| ITF M25 Maribor | 2023/09/04 09:35 | Thomas Rohseano v Enrico Giacomini | 1-6,0-6 |
| ITF M15 Forli | 2023/08/30 11:30 | Francesco Forti v Enrico Giacomini | 6-2,7-5 |
| ITF M15 Forli | 2023/08/29 11:50 | Omar Brigida v Enrico Giacomini | 3-6,5-7 |
| ITF M15 Forli | 2023/08/27 13:00 | Enrico Giacomini v Marco De Rossi | 6-2,6-4 |
| ITF M15 Caslano | 2023/08/21 11:30 | Enrico Giacomini v Davide Ferrarolli | 7-6,4-6,6-10 |