Stadium: Court 4 Round: 19 Ground: Hardcourt outdoor
| ITF M15 Limassol | 2023/11/23 11:05 | Jack Karlsson Winstrand v Max Dahlin | 2-6,4-6 |
| 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 Thurner, Dean | 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 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 M15 Limassol | 2023/11/27 08:00 | Nicholas Campbell v Mihail Ivanov | 3-6,6-4,4-10 |
| ITF M15 Limassol | 2023/11/20 08:00 | Mihail Ivanov v Mats Bredschneijder | 2-6,2-6 |
| ITF M25 Heraklion | 2023/11/05 07:00 | Graham Maassen v Mihail Ivanov | 6-2,6-4 |
| ITF M25 Heraklion | 2023/10/29 09:00 | Mihail Ivanov v William Norton | 3-6,4-6 |
| ITF M25 Pazardzhik | 2023/10/04 06:55 | Mihail Ivanov v Nikola Kolyachev | 4-6,2-6 |
| ITF M25 Pazardzhik | 2023/10/02 12:25 | Mihail Ivanov v Mykyta Riepkin | 6-4,6-2 |
| ITF M25 Pazardzhik | 2023/09/27 09:50 | Nicholas David Ionel v Mihail Ivanov | 6-1,6-3 |
| ITF M25 Pazardzhik | 2023/09/25 10:00 | Mihail Ivanov v Shendrit Deari | 0-6,6-3,10-8 |