Stadium: Court 1 Round: 44 Ground: Hardcourt outdoor
| 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 Sharm El Sheikh | 2023/03/21 09:35 | Chukang Wang v Jack Karlsson Winstrand | 6-4,6-3 |
| ITF M15 Sharm El Sheikh | 2023/03/19 13:00 | Pavlo Rezoglazov v Jack Karlsson Winstrand | 1-6,0-6 |