Stadium: Indoor 12 Round: 25 Ground: Hardcourt outdoor
| Challenger Zhangjiagang | 2023/08/28 07:00 | Matthew Romios v Leonid Sheyngezikht | 4-6,6-3,4-6 |
| Challenger Zhangjiagang | 2023/08/27 03:30 | Leonid Sheyngezikht v Xiaofei Wang | 6-4,6-3 |
| ITF M25 Tainan | 2023/08/22 02:00 | Naoki Tajima v Leonid Sheyngezikht | 3-6,5-7 |
| ITF M25 Tainan | 2023/08/16 06:05 | Leonid Sheyngezikht v Chen-Yu Lu | 6-2,4-6,3-6 |
| ITF M15 Hyvinkaa | 2023/08/03 10:10 | Karl Friberg v Leonid Sheyngezikht | 6-2,7-6 |
| Challenger Astana | 2023/07/23 09:15 | Sidharth Rawat v Leonid Sheyngezikht | 6-2,6-2 |
| ITF M25 Arlon | 2023/06/28 14:55 | Leonid Sheyngezikht v Tibo Colson | 0-6,0-6 |
| ITF M25 Arlon | 2023/06/27 11:00 | Leonid Sheyngezikht v Thorben Sannen | 6-3,6-2 |
| Challenger Prague | 2023/08/23 09:45 | Federico Agustin Gomez v Lorenzo Giustino | 6-3,6-3 |
| Challenger Prague | 2023/08/21 11:50 | Lorenzo Giustino v Filip Cristian Jianu | 6-4,6-3 |
| Challenger Todi | 2023/08/15 16:35 | Lorenzo Giustino v Mathys Erhard | 6-7,0-6 |
| Challenger Porto | 2023/08/01 14:50 | Antoine Escoffier v Lorenzo Giustino | 6-3,6-4 |
| Challenger Pozoblanco | 2023/07/18 07:30 | Lorenzo Giustino v Edas Butvilas | 1-6,2-6 |
| Challenger Salzburg | 2023/07/10 10:30 | Lorenzo Giustino v Sandro Kopp | 0-6,2-6 |
| Challenger Troyes | 2023/07/07 15:30 | Calvin Hemery v Lorenzo Giustino | 6-4,4-6,6-1 |
| Challenger Troyes | 2023/07/06 11:00 | Lucas Gerch v Lorenzo Giustino | 3-6,6-3,3-6 |