Stadium: Court 2 Round: 25 Ground: Clay
| Challenger Skopje | 2023/05/24 09:00 | Max Houkes v Oliver Crawford | 4-6,2-6 |
| Challenger Skopje | 2023/05/22 15:10 | Kacper Zuk v Max Houkes | 1-6,1-6 |
| Challenger Tunis | 2023/05/16 08:30 | Sho Shimabukuro v Max Houkes | 6-1,3-6,6-1 |
| Challenger Tunis | 2023/05/14 13:50 | Rayen Hermassi v Max Houkes | 2-6,0-6 |
| Challenger Prague | 2023/05/01 11:05 | Max Houkes v Vitaliy Sachko | 6-4,4-6,5-7 |
| Challenger Prague | 2023/04/30 12:30 | Shintaro Mochizuki v Max Houkes | 6-7,3-6 |
| Challenger Rome | 2023/04/28 09:30 | Sumit Nagal v Max Houkes | 7-5,6-0 |
| Challenger Rome | 2023/04/27 09:00 | Max Houkes v Jelle Sels | 6-4,7-6 |
| 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 Telde | 2023/04/09 09:00 | Yannick Penkner v Jack Karlsson Winstrand | 6-3,7-6 |