Stadion: Court 3 Round: 26 Ground: Hardcourt indoor
| Challenger - Bratislava | 2023/10/11 10:35 | Akira Santillan v Martin Damm | 3-6,6-3,3-6 |
| Challenger - Bratislava | 2023/10/09 10:15 | Joao Sousa v Martin Damm | 3-6,7-6,1-6 |
| Challenger - Bratislava | 2023/10/08 11:40 | Viktor Durasovic v Martin Damm | 6-7,2-6 |
| Challenger - Alicante | 2023/10/06 10:00 | Martin Damm v Maximilian Marterer | 5-7,5-7 |
| Challenger - Alicante | 2023/10/04 10:00 | Benoit Paire v Martin Damm | 2-6,3-6 |
| Challenger - Alicante | 2023/10/03 09:00 | Martin Damm v Alberto Barroso Campos | 6-4,7-6 |
| Challenger - Alicante | 2023/10/02 09:00 | Martin Damm v Svyatoslav Gulin | 6-3,6-1 |
| Challenger - Alicante | 2023/10/01 11:25 | Martin Damm v Alejandro Manzanera Pertusa | 6-7,6-4,6-4 |
| 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 - Setúbal | 2023/09/22 10:00 | Jaime Faria v Kalin Ivanovski | 6-4,6-4 |
| ITF - M25 - Setúbal | 2023/09/21 12:30 | Francisco Rocha v Kalin Ivanovski | 6-7,3-6 |
| ITF - M25 - Setúbal | 2023/09/19 12:20 | Sascha Gueymard Wayenburg v Kalin Ivanovski | 4-6,4-6 |
| ITF - M25 - Sintra | 2023/09/14 09:00 | Duarte Vale v Kalin Ivanovski | 7-6,6-4 |
| ITF - M25 - Sintra | 2023/09/13 14:15 | Marcus Walters v Kalin Ivanovski | 4-6,6-7 |