Stadium: Court 2 Round: 62 Ground: Hardcourt outdoor
| ITF M25 Tavira | 2023/10/08 14:30 | Tomas Cortez v Jasin Jakupi | 6-4,6-1 |
| ITF M25 Pazardzhik | 2023/10/03 06:30 | Alvaro Bueno Gil v Jasin Jakupi | 7-5,6-3 |
| ITF M25 Pazardzhik | 2023/10/02 09:00 | Jasin Jakupi v Edoardo L Cattaneo | 6-2,6-2 |
| ITF M15 Buschhausen | 2023/09/11 08:00 | Yan Sabanin v Jasin Jakupi | 6-3,6-3 |
| ITF M15 Buschhausen | 2023/09/10 14:30 | Temurmalik Amirov v Jasin Jakupi | 3-6,0-6 |
| ITF M15 Haren | 2023/09/03 08:00 | Jasin Jakupi v Mats Bredschneijder | 2-6,3-6 |
| Davis Cup | 2023/07/29 08:00 | Jasin Jakupi v Damien Gelabert | 6-3,6-0 |
| Davis Cup | 2023/07/28 08:00 | Martin Muedini v Jasin Jakupi | 0-6,0-6 |
| ITF M25 Tavira | 2023/10/12 09:00 | Aleksandr Braynin v Simon Freund | 6-4,6-4 |
| ITF M25 Tavira | 2023/10/11 08:30 | Simon Freund v Diogo Marques | 6-3,7-6 |
| ITF M25 Tavira | 2023/10/10 08:30 | Alexis Boureau v Simon Freund | 3-6,1-6 |
| ITF M25 Tavira | 2023/10/09 09:00 | Tiago Boschmans v Simon Freund | 0-6,1-6 |
| ITF M25 Tavira | 2023/10/08 11:30 | Rafael Giotis v Simon Freund | 3-6,5-7 |
| ITF M25 Falun | 2023/09/25 07:55 | Jonas Trinker v Simon Freund | 5-7,6-1,10-2 |
| ITF M25 Falun | 2023/09/24 10:00 | Fabian Hansch Mauritzson v Simon Freund | 1-6,6-7 |
| ITF M15 Danderyd | 2023/09/20 09:55 | Simon Freund v Tibo Colson | 3-6,4-6 |