Stadium: Court B Round: 14 Ground: Hardcourt indoor
| Challenger Bergamo | 2023/10/30 09:00 | Mikhail Kukushkin v Kalin Ivanovski | 3-6,7-6,6-4 |
| Challenger Bergamo | 2023/10/29 09:00 | Alessio Balestrieri v Kalin Ivanovski | 2-6,1-6 |
| Challenger Hamburg | 2023/10/16 14:00 | Kalin Ivanovski v Jelle Sels | 2-6,4-6 |
| Challenger Bratislava | 2023/10/12 09:00 | Martin Damm v Kalin Ivanovski | 6-3,6-4 |
| Challenger Bratislava | 2023/10/10 10:40 | Kalin Ivanovski v Peter Gojowczyk | 7-6,6-2 |
| Challenger Bratislava | 2023/10/09 08:30 | Mate Valkusz v Kalin Ivanovski | 3-6,5-7 |
| Challenger Bratislava | 2023/10/08 12:25 | Peter Nad v Kalin Ivanovski | 7-6,2-6,0-6 |
| ITF M25 Setubal | 2023/09/22 10:00 | Jaime Faria v Kalin Ivanovski | 6-4,6-4 |
| Challenger Matsuyama | 2023/11/05 01:00 | Yan Bai v Ryuki Matsuda | 6-2,6-4 |
| Challenger Ortisei | 2023/10/23 10:40 | Luca Giacomini v Ryuki Matsuda | 7-5,6-3 |
| Challenger Ortisei | 2023/10/22 12:05 | Samir Hamza Reguig v Ryuki Matsuda | 2-6,2-6 |
| ITF M25 Santa Margherita | 2023/10/16 11:30 | Felix Gill v Ryuki Matsuda | 6-1,6-2 |
| ITF M25 Santa Margherita | 2023/10/11 10:35 | Ryuki Matsuda v Salvatore Caruso | 3-6,6-1,2-6 |
| ITF M25 Santa Margherita | 2023/10/09 14:20 | Benjamin Loccisano v Ryuki Matsuda | 3-6,3-6 |
| ITF M25 Santa Margherita | 2023/10/04 08:00 | Giuseppe La Vela v Ryuki Matsuda | 6-0,6-4 |
| ITF M25 Santa Margherita | 2023/10/03 11:05 | Ryuki Matsuda v Fausto Tabacco | 6-3,6-2 |