Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| ITF M15 Limassol | 2023/11/22 10:00 | Sergis Kyratzis v Jack Karlsson Winstrand | 6-4,4-6,4-6 |
| ITF M15 Limassol | 2023/11/20 10:30 | Jack Karlsson Winstrand v Dean Thurner | 6-0,7-6 |
| ITF M25 Dharwad | 2023/10/16 07:00 | Jack Karlsson Winstrand v Enrico Giacomini | 4-6,6-1,6-10 |
| 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 M15 Limassol | 2023/11/21 11:00 | Daniel De Jonge v Max Dahlin | 6-7,1-6 |
| Challenger Danderyd | 2023/11/14 15:45 | Jakub Mensik v Max Dahlin | 6-2,7-6 |
| ITF M25 Mulhouse | 2023/11/02 11:35 | Max Dahlin v Nikolay Vylegzhanin | 4-6,5-7 |
| ITF M25 Mulhouse | 2023/10/31 08:55 | Sascha Gueymard Wayenburg v Max Dahlin | 6-7,3-6 |
| ITF M25 Mulhouse | 2023/10/30 12:00 | Max Dahlin v Oscar Houille | 6-0,6-1 |
| ITF M25 Mulhouse | 2023/10/29 10:50 | Max Dahlin v Antonin Witz | 6-0,6-2 |
| ITF M15 Villers Les Nancy | 2023/10/19 13:05 | Max Dahlin v Amaury Raynel | 0-6,3-6 |
| ITF M15 Villers Les Nancy | 2023/10/17 10:55 | Maxime Mora v Max Dahlin | 4-6,6-7 |