Stadium: Court 4 Round: 44 Ground: Clay
| ITF M15 Osijek | 2023/05/01 11:30 | Dennis Dragomirov v Maj Premzl | 5-7,0-6 |
| ITF M15 Osijek | 2023/04/30 11:00 | Martin Benes v Dennis Dragomirov | 5-7,6-2,7-10 |
| ITF M15 Sharm El Sheikh | 2023/03/12 08:00 | Dennis Dragomirov v Samuel Puskar | 1-6,5-7 |
| ITF M15 Sharm El Sheikh | 2023/03/05 10:00 | Dennis Dragomirov v Hamish Stewart | 3-6,0-6 |
| ITF M15 Sharm El Sheikh | 2023/02/26 11:30 | Gabriele Bosio v Dennis Dragomirov | 3-6,6-3,10-7 |
| ITF M15 Sharm El Sheikh | 2023/02/19 08:00 | Dennis Dragomirov v Pijus Vaitiekunas | 4-6,2-6 |
| ITF M15 Sharm El Sheikh | 2022/09/25 09:00 | Dennis Dragomirov v Stefan Simeunovic | 3-6,1-6 |
| ITF M25 Madrid | 2022/09/12 10:00 | Luis Diego Chavez Villalpando v Dennis Dragomirov | 2-6,6-4,10-6 |
| ITF M15 Osijek | 2023/05/02 09:45 | Radomir Tomic v Lucio Carnevalle | 5-7,6-2,8-10 |
| ITF M15 Osijek | 2023/05/01 10:10 | Radomir Tomic v Alen Bill | 6-0,6-3 |
| ITF M15 Osijek | 2023/04/30 11:00 | Radomir Tomic v Dean Thurner | 6-2,6-0 |
| UTR Pro Beograd | 2023/04/22 07:30 | Aleksa Mardjonovic v Radomir Tomic | 6-2,6-2 |
| UTR Pro Beograd | 2023/04/20 06:00 | Radomir Tomic v Petr Nesterov | 6-3,0-6,7-5 |
| UTR Pro Beograd | 2023/04/19 08:05 | Radomir Tomic v Christos Keisidis | 6-0,6-2 |
| UTR Pro Beograd | 2023/04/18 06:00 | Radomir Tomic v Vanja Hodzic | 6-3,2-6,7-5 |
| UTR Pro Beograd | 2023/04/17 08:55 | Radomir Tomic v Viktor Jovic | 3-6,3-6 |