Stadium: Court 4 Round: 54 Ground: Clay
| 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 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 Vejle | 2023/07/24 07:00 | Pierre Gimla v Gabriel Matuszewski | 0-6,0-6 |
| ITF M25 Roehampton | 2023/07/16 10:40 | Sean Hodkin v Gabriel Matuszewski | 6-4,6-2 |
| ITF M25 Marburg | 2023/07/04 10:05 | Dominik Recek v Gabriel Matuszewski | 6-2,6-1 |
| ITF M25 Marburg | 2023/07/03 08:00 | Manuel Almeida v Gabriel Matuszewski | 3-6,2-6 |
| ITF M15 Wroclaw | 2023/06/27 09:40 | Gabriel Matuszewski v Jiri Barnat | 2-6,2-6 |
| ITF M15 Kursumlijska Banja | 2023/06/19 07:30 | Gabriel Matuszewski v Dimitrije Zubac | 6-7,6-4,8-10 |
| ITF M15 Kursumlijska Banja | 2023/06/18 07:00 | Gabriel Matuszewski v Nikola Kolyachev | 6-4,6-4 |
| ITF M15 Kursumlijska Banja | 2023/06/11 12:30 | Gabriel Matuszewski v Marko Maksimovic | 1-6,1-6 |