Stadium: Center Court Round: 26 Ground: Clay
| Iasi, Romania | 2023/07/10 16:10 | Enzo Couacaud v Filip Cristian Jianu | 2-6,1-6 |
| ITF M25 Brasov | 2023/07/05 07:00 | Filip Cristian Jianu v Francesco Ferrari | 6-1,6-1 |
| Challenger Modena | 2023/06/26 14:30 | Filip Cristian Jianu v Gianmarco Ferrari | 7-6,4-6,4-6 |
| Challenger Blois | 2023/06/19 17:05 | Filip Cristian Jianu v Kimmer Coppejans | 5-7,2-6 |
| ITF M15 Rabat | 2023/06/14 13:35 | Filip Cristian Jianu v Ahouda, Walid | 1-6,4-6 |
| Tanger, Singles M-ITF-MAR-01A | 2023/06/10 09:30 | Filip Cristian Jianu v Corentin Denolly | 5-7,6-0,2-6 |
| Tanger, Singles M-ITF-MAR-01A | 2023/06/09 09:00 | Filip Cristian Jianu v Guido Ivan Justo | 3-6,6-0,6-1 |
| Tanger, Singles M-ITF-MAR-01A | 2023/06/08 11:10 | Filip Cristian Jianu v Andrea Bacaloni | 6-3,6-0 |
| Iasi, Romania | 2023/07/11 15:30 | Ivanovski, Kalin v Nicholas David Ionel | 4-6,7-6,6-2 |
| Iasi, Romania | 2023/07/10 08:20 | Ivanovski, Kalin v Dan Alexandru Tomescu | 7-6,7-6 |
| Iasi, Romania | 2023/07/09 10:20 | Ivanovski, Kalin v Brandon Walkin | 6-2,6-2 |
| Challenger Troyes | 2023/07/02 12:10 | Ivanovski, Kalin v Giuseppe Tresca | 4-6,6-7 |
| Poznan, Poland | 2023/06/18 08:30 | Kai Wehnelt v Ivanovski, Kalin | 6-3,3-6,6-3 |
| Coupe Davis | 2023/06/15 10:00 | Ivanovski, Kalin v Cozbinov, Alexander | 5-7,2-5 |
| Coupe Davis | 2023/06/14 10:35 | Ivanovski, Kalin v Liam Delicata | 6-2,6-4 |
| ITF M25 Skopje | 2023/06/11 11:00 | Ivanovski, Kalin v Sascha Gueymard Wayenburg | 7-6,6-4 |