Stadium: Court Center Round: 54 Ground: Hardcourt outdoor
| ITF M25 Telfs | 2022/07/11 11:00 | Dennis Dragomirov v Jakub Kroslak | 3-6,6-4,5-10 |
| ITF M25 Telfs | 2022/07/11 07:30 | Pietro Pampanin v Dennis Dragomirov | 1-6,7-5,8-10 |
| ITF M25 Telfs | 2022/07/10 08:00 | Niklas Waldner v Dennis Dragomirov | 3-6,5-7 |
| ITF M25 Wroclaw | 2022/06/27 08:00 | Michal Mikula v Dennis Dragomirov | 7-5,6-2 |
| ITF M25 Wroclaw | 2022/06/26 10:30 | Dennis Dragomirov v Michal Matuszewski | 4-6,6-4,10-3 |
| ITF M15 Skopje | 2022/06/13 08:00 | Franco Roncadelli v Dennis Dragomirov | 6-1,6-3 |
| ITF M15 Budva | 2022/06/06 08:00 | Dennis Dragomirov v Petar Jovanovic | 2-6,1-6 |
| ITF M15 Budva | 2022/05/29 09:30 | Maurus Malgiaritta v Dennis Dragomirov | 6-4,6-2 |
| ITF M25 Edwardsville | 2022/07/25 14:00 | Nishanth Basavareddy v Stefan Simeunovic | 6-7,0-6 |
| ITF M25 Champaign | 2022/07/18 15:00 | Justin Boulais v Stefan Simeunovic | 6-2,6-2 |
| ITF M15 South Bend | 2022/06/22 15:40 | Stefan Simeunovic v Joe Tyler | 6-4,5-7,2-6 |
| ITF M15 South Bend | 2022/06/21 12:30 | Stefan Simeunovic v A.trice Pickens | 2-6,3-6 |
| ITF M15 South Bend | 2022/06/20 15:00 | Stefan Simeunovic v Nishanth Basavareddy | 7-6,6-3 |
| UTR Pro Tennis Series Manzanillo | 2022/06/11 14:00 | Stefan Simeunovic v Delmas N'tcha | 6-4,1-4 |
| UTR Pro Tennis Series Manzanillo | 2022/06/10 14:00 | Federico Zeballos v Stefan Simeunovic | 6-2,6-2 |
| UTR Pro Tennis Series Manzanillo | 2022/06/09 16:51 | Georgios Nouchakis v Stefan Simeunovic | 5-7,7-5,5-6 |