Stadium: Court 2 Round: 54 Ground: Clay
| ITF M25 Risskov/Aarhus | 2023/06/14 08:30 | Max Houkes v Jack Karlsson Winstrand | 7-5,6-2 |
| 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 Saarlouis | 2023/06/18 12:00 | Jeffrey Von Der Schulenburg v Ruben Hartig | 6-1,6-0 |
| ITF M25 Risskov/Aarhus | 2023/06/11 13:25 | Ruben Hartig v Gianluca Cadenasso | 4-6,2-6 |
| ITF M15 Constanta | 2023/05/29 11:00 | Nicolas Bruna v Ruben Hartig | 7-5,7-6 |
| ITF M15 Constanta | 2023/05/28 14:00 | Alexandru Luca v Ruben Hartig | 4-6,3-6 |
| ITF M15 Meerbusch | 2023/04/24 10:00 | Ruben Hartig v Olivier Rojas | 6-4,6-4 |
| ITF M15 Meerbusch | 2023/04/24 08:00 | Leopold Zima v Ruben Hartig | 6-4,6-1 |
| ITF M15 Antalya | 2023/04/17 12:15 | Marlon Vankan v Ruben Hartig | 6-3,6-3 |
| ITF M15 Antalya | 2023/04/16 07:00 | Ruben Hartig v Pavel Gula | 6-1,6-3 |