Stadium: Court 5 Round: 54 Ground: Hardcourt indoor
| 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 |
| ITF M25 Varnamo | 2023/05/08 10:25 | Jack Karlsson Winstrand v Eliot Nobel | 6-1,6-2 |
| ITF M15 Telde | 2023/04/16 07:00 | Ian Luca Cervantes Tomas v Jack Karlsson Winstrand | 7-6,0-6,10-8 |
| ITF M15 Telde | 2023/04/09 09:00 | Yannick Penkner v Jack Karlsson Winstrand | 6-3,7-6 |
| 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 |