Stadium: Schoonderbeekbouw Court Round: 14 Ground: Clay
| ITF M25 Kassel | 2023/07/13 14:25 | Ryan Nijboer v Andrew Paulson | 6-7,4-6 |
| ITF M25 Kassel | 2023/07/11 14:45 | Ryan Nijboer v Viacheslav Bielinskyi | 6-2,6-2 |
| ITF M25 Haag | 2023/07/07 16:30 | Guy Den Ouden v Ryan Nijboer | 6-1,6-2 |
| ITF M25 Haag | 2023/07/06 14:05 | Aleksandr Braynin v Ryan Nijboer | 4-6,6-7 |
| ITF M25 Haag | 2023/07/05 15:15 | Felix Corwin v Ryan Nijboer | 3-6,4-6 |
| ITF M15 Alkmaar | 2023/06/30 12:05 | Ryan Nijboer v Sander Jong | 3-6,4-6 |
| ITF M15 Alkmaar | 2023/06/29 10:30 | Ryan Nijboer v Teun Rozenberg | 6-4,6-7,6-3 |
| ITF M15 Alkmaar | 2023/06/28 11:40 | Ryan Nijboer v Nicolas Kobelt | 6-2,6-1 |
| Challenger Braunschweig | 2023/07/10 11:50 | Yanaki Milev v Denis Yevseyev | 6-7,6-3,3-6 |
| Challenger Braunschweig | 2023/07/09 14:30 | Alvaro Lopez San Martin v Yanaki Milev | 6-3,6-7,4-6 |
| ITF M25 Marburg | 2023/07/05 14:40 | Michael Agwi v Yanaki Milev | 7-5,6-3 |
| Challenger Parma | 2023/06/18 08:00 | Yanaki Milev v Akira Santillan | 1-6,6-4,6-7 |
| ITF M25 Skopje | 2023/06/06 11:05 | Yanaki Milev v Neil Oberleitner | 4-6,4-6 |
| Challenger Skopje | 2023/05/21 09:50 | Yanaki Milev v Pedro Boscardin Dias | 2-6,6-7 |
| ITF M15 - Antalya | 2023/05/11 07:30 | Deney Wassermann v Yanaki Milev | 6-3,2-6,6-2 |
| ITF M15 - Antalya | 2023/05/10 12:20 | Lorenzo Joaquin Rodriguez v Yanaki Milev | 4-6,3-6 |