Stadium: Court 2 Round: 26 Ground: Clay
| ITF M25 Kursumlijska Banja | 2023/05/10 07:00 | Timo Legout v Mikalai Haliak | 6-2,7-6 |
| ITF M25 Angers | 2023/04/20 09:00 | Timo Legout v Pierre Delage | 0-6,5-7 |
| ITF M25 Angers | 2023/04/19 13:50 | Timo Legout v Mirko Martinez | 4-6,6-4,6-3 |
| ITF M25 Santa Margherita | 2023/04/08 09:00 | Daniel Michalski v Timo Legout | 6-4,6-3 |
| ITF M25 Santa Margherita | 2023/04/07 09:30 | Gianmarco Ferrari v Timo Legout | 6-7,1-6 |
| ITF M25 Santa Margherita | 2023/04/06 08:30 | Timo Legout v Fabrizio Andaloro | 6-1,7-5 |
| ITF M25 Santa Margherita | 2023/04/04 12:00 | Timo Legout v Mateo Nicolas Martinez | 6-1,7-5 |
| ITF M25 Palmanova | 2023/03/21 14:50 | Felix Gill v Timo Legout | 7-6,6-4 |
| ITF M25 Kursumlijska Banja | 2023/05/10 09:00 | Kalin Ivanovski v Viktor Jovic | 3-6,6-3,6-4 |
| Challenger Prague | 2023/05/01 13:00 | Kalin Ivanovski v Dominic Stephan Stricker | 2-6,2-6 |
| Challenger Oeiras | 2023/04/16 12:30 | Billy Harris v Kalin Ivanovski | 6-2,4-6,6-4 |
| Challenger Split | 2023/04/11 12:20 | Duje Ajdukovic v Kalin Ivanovski | 6-7,6-1,6-1 |
| ITF M25 Dubrovnik | 2023/04/06 08:00 | Aldin Setkic v Kalin Ivanovski | 7-6,6-2 |
| ITF M25 Dubrovnik | 2023/04/05 07:00 | Matteo Donati v Kalin Ivanovski | 6-1,3-6,0-6 |
| ITF M25 Toulouse | 2023/03/23 10:00 | Kalin Ivanovski v Harry Wendelken | 1-6,6-7 |
| ITF M25 Toulouse | 2023/03/21 13:00 | Kalin Ivanovski v Paul Inchauspe | 6-2,6-4 |