Stadium: Hard 21 Round: 62 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/26 08:30 | Patrick Toman v Evgenios Vasilakis | 2-6,3-6 |
| ITF M15 Heraklion | 2023/10/15 07:00 | Evgenios Vasilakis v Dario Huber | 3-6,2-6 |
| ITF M25 Heraklion | 2023/11/27 08:00 | Brett Winters v Dennis Dragomirov | 5-7,1-6 |
| ITF M15 Heraklion | 2023/11/20 10:00 | Dennis Dragomirov v Vasil Yehorov | 6-3,3-6,9-11 |
| ITF M15 Heraklion | 2023/11/19 07:00 | Tomas Krcma v Dennis Dragomirov | 2-6,0-6 |
| UTR Pro Olomouc | 2023/11/12 07:00 | Dennis Dragomirov v Jiri Cizek | 6-3,6-4 |
| UTR Pro Olomouc | 2023/11/11 07:00 | Domagoj Biljesko v Dennis Dragomirov | 3-6,6-7 |
| UTR Pro Olomouc | 2023/11/10 09:48 | Dennis Dragomirov v Oleg Prihodko | 2-6,3-6 |
| UTR Pro Olomouc | 2023/11/09 10:00 | Dennis Dragomirov v Jakub Vrba | 6-3,7-5 |
| UTR Pro Olomouc | 2023/11/08 07:00 | Christos Keisidis v Dennis Dragomirov | 5-7,3-6 |