Stadion: Center Court Round: 26 Ground: Clay
| Challenger - Iasi | 2023/07/10 16:10 | Enzo Couacaud v Filip Cristian Jianu | 2-6,1-6 |
| ITF - M25 - Brașov | 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 Walid Ahouda | 1-6,4-6 |
| ITF - M15 - Tanger | 2023/06/10 09:30 | Filip Cristian Jianu v Corentin Denolly | 5-7,6-0,2-6 |
| ITF - M15 - Tanger | 2023/06/09 09:00 | Filip Cristian Jianu v Guido Ivan Justo | 3-6,6-0,6-1 |
| ITF - M15 - Tanger | 2023/06/08 11:10 | Filip Cristian Jianu v Andrea Bacaloni | 6-3,6-0 |
| Challenger - Iasi | 2023/07/11 15:30 | Kalin Ivanovski v Nicholas David Ionel | 4-6,7-6,6-2 |
| Challenger - Iasi | 2023/07/10 08:20 | Kalin Ivanovski v Dan Alexandru Tomescu | 7-6,7-6 |
| Challenger - Iasi | 2023/07/09 10:20 | Kalin Ivanovski v Brandon Walkin | 6-2,6-2 |
| Challenger - Troyes | 2023/07/02 12:10 | Kalin Ivanovski v Giuseppe Tresca | 4-6,6-7 |
| Challenger - Posen | 2023/06/18 08:30 | Kai Wehnelt v Kalin Ivanovski | 6-3,3-6,6-3 |
| Davis Cup | 2023/06/15 10:00 | Kalin Ivanovski v Alexander Cozbinov | 5-7,2-5 |
| Davis Cup | 2023/06/14 10:35 | Kalin Ivanovski v Liam Delicata | 6-2,6-4 |
| ITF - M25 - Skopje | 2023/06/11 11:00 | Kalin Ivanovski v Sascha Gueymard Wayenburg | 7-6,6-4 |