Stadium: Court 5 Round: 54 Ground: Hardcourt indoor
| ITF M15 Szczawno | 2023/08/31 12:00 | Karol Filar v Jack Karlsson Winstrand | 6-4,3-6,6-2 |
| ITF M15 Szczawno | 2023/08/30 11:50 | Jack Karlsson Winstrand v Maxime Mora | 1-6,6-4,6-4 |
| ITF M15 Szczawno | 2023/08/29 09:30 | Jack Karlsson Winstrand v Henrik Bladelius | 6-4,5-7,10-4 |
| ITF M25 Ystad | 2023/08/15 12:30 | Andrea Gola v Jack Karlsson Winstrand | 6-3,6-3 |
| ITF M15 Hyvinkaa | 2023/08/01 07:00 | Lucio Carnevalle v Jack Karlsson Winstrand | 3-6,6-2,10-3 |
| ITF M15 Hyvinkaa | 2023/07/31 07:00 | Kenzo K Larsson v Jack Karlsson Winstrand | 4-6,5-7 |
| ITF M15 Vejle | 2023/07/26 07:00 | Leonardo Rossi v Jack Karlsson Winstrand | 6-4,3-6,6-3 |
| ITF M15 Vejle | 2023/07/25 07:00 | Jack Karlsson Winstrand v Gabriel Matuszewski | 6-2,6-4 |
| ITF M15 Addis Ababa | 2023/05/23 07:00 | Tsegai Gebremeskel v Ben Weintraub | 1-6,1-6 |
| ITF M15 Addis Ababa | 2023/05/14 07:00 | Yash Chaurasia v Tsegai Gebremeskel | 6-1,6-4 |
| ITF M25 Varnamo | 2023/05/08 13:45 | Tsegai Gebremeskel v Eldin Nokic | 6-2,0-6,8-10 |