Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| 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 Kamen | 2023/06/26 10:00 | Jack Karlsson Winstrand v Ruben Hartig | 0-6,1-6 |
| 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 M15 Vejle | 2023/07/25 10:05 | Patrick Kaukovalta v Max Dahlin | 2-6,6-4,6-2 |
| ATP Bastad | 2023/07/17 08:00 | Pavel Kotov v Max Dahlin | 6-4,6-4 |
| ITF M15 Vaasa | 2023/06/07 12:10 | Luca Giacomini v Max Dahlin | 6-3,6-4 |
| ITF M15 Kalmar | 2023/05/21 08:55 | Max Dahlin v Lucas Catarina | 1-6,6-3,6-7 |
| ITF M15 Kalmar | 2023/05/20 10:30 | Alexander Blockx v Max Dahlin | 2-6,6-3,4-6 |
| ITF M15 Kalmar | 2023/05/19 11:05 | Max Dahlin v Filip Bergevi | 7-6,2-6,7-6 |
| ITF M15 Kalmar | 2023/05/18 10:20 | Max Dahlin v Adam Heinonen | 6-3,2-6,6-4 |
| ITF M15 Kalmar | 2023/05/16 12:45 | Harry Wendelken v Max Dahlin | 6-4,3-6,6-7 |