Stadium: Court 4 Round: 25 Ground: Carpet indoor
| ITF M15 Cadolzburg | 2024/01/15 10:00 | Laurin Aerne v Jack Karlsson Winstrand | 4-6,4-6 |
| ITF M15 Cadolzburg | 2024/01/14 11:30 | Gabriel Moroder v Jack Karlsson Winstrand | 2-6,4-6 |
| ITF M15 Limassol | 2023/11/29 12:35 | Jack Karlsson Winstrand v William Jucha | 2-6,3-6 |
| ITF M15 Limassol | 2023/11/28 08:00 | Jack Karlsson Winstrand v Mihail Ivanov | 6-2,6-2 |
| ITF M15 Limassol | 2023/11/23 11:05 | Jack Karlsson Winstrand v Max Dahlin | 2-6,4-6 |
| ITF M15 Limassol | 2023/11/22 10:00 | Sergis Kyratzis v Jack Karlsson Winstrand | 6-4,4-6,4-6 |
| ITF M15 Limassol | 2023/11/20 10:30 | Jack Karlsson Winstrand v Dean Thurner | 6-0,7-6 |
| ITF M25 Dharwad | 2023/10/16 07:00 | Jack Karlsson Winstrand v Enrico Giacomini | 4-6,6-1,6-10 |
| German Championship | 2023/12/07 12:00 | Tom Gentzsch v Max Hans Rehberg | 2-6,7-5,3-6 |
| German Championship | 2023/12/06 12:05 | Luca Matteo Sobbe v Tom Gentzsch | 3-6,2-6 |
| Challenger Maia | 2023/11/29 15:25 | Fabio Fognini v Tom Gentzsch | 6-7,6-3,7-5 |
| Challenger Maia | 2023/11/27 11:00 | Miguel Damas v Tom Gentzsch | 6-2,3-6,1-6 |
| Challenger Maia | 2023/11/26 11:00 | Federico Bertuccioli v Tom Gentzsch | 4-6,2-6 |
| ITF M15 Monastir | 2023/11/15 08:30 | Tom Gentzsch v Nikola Basic | 6-4,1-6,3-6 |
| ITF M15 Monastir | 2023/11/10 09:00 | Juan Bautista Otegui v Tom Gentzsch | 6-3,6-4 |
| ITF M15 Monastir | 2023/11/09 08:30 | Nicolas Kobelt v Tom Gentzsch | 5-7,1-6 |