Stadium: Court 1 Round: 54 Ground: Clay
| 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 |
| ITF M15 Sharm El Sheikh | 2023/03/13 08:00 | Jack Karlsson Winstrand v Hamish Stewart | 1-6,3-6 |
| ITF M15 Sharm El Sheikh | 2023/03/12 08:00 | Mohamad Gomaa v Jack Karlsson Winstrand | 0-6,4-6 |
| ITF M25 Bath | 2023/02/06 11:40 | Sean Hodkin v Jack Karlsson Winstrand | 6-4,6-2 |
| ITF M25 Varnamo | 2023/05/08 09:45 | Rafael Ymer v Felipe Mikkelsen | 4-6,7-6,10-5 |