Stadium: CC - Ct 2 Round: 25 Ground: Clay
| ITF M15 Duffel | 2023/06/15 10:00 | Ryan Nijboer v Andrea Gola | 2-6,6-1,6-3 |
| ITF M15 Duffel | 2023/06/13 08:00 | Otakar Ungerman v Andrea Gola | 4-6,3-6 |
| ITF M15 Duffel | 2023/06/12 08:00 | Andrea Gola v David Quayle | 6-1,6-2 |
| Challenger Turin | 2023/05/15 10:35 | Federico Gaio v Andrea Gola | 6-2,6-3 |
| Challenger Turin | 2023/05/14 10:00 | Andrea Gola v David Pichler | 6-4,6-4 |
| ITF M25 Varnamo | 2023/05/12 08:15 | Andrea Gola v Eric Vanshelboim | 4-6,1-6 |
| ITF M25 Varnamo | 2023/05/11 10:05 | Andrea Gola v Vito Tonejc | 6-2,6-0 |
| ITF M25 Varnamo | 2023/05/10 11:00 | Karl Friberg v Andrea Gola | 4-6,3-6 |
| 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 Telde | 2023/04/16 07:00 | Ian Luca Cervantes Tomas v Jack Karlsson Winstrand | 7-6,0-6,10-8 |