Stadium: Court 4 Oberhaching Round: 44 Ground: Hardcourt indoor
| ITF M15 Oberhaching | 2022/02/13 08:00 | Dusan Obradovic v Kai Lemstra | 1-6,6-4,10-8 |
| ITF M25 Monastir | 2022/01/12 08:00 | Taiyo Yamanaka v Dusan Obradovic | 7-5,6-1 |
| ITF M25 Monastir | 2022/01/06 08:00 | Giovanni Oradini v Dusan Obradovic | 6-4,6-2 |
| ITF M25 Monastir | 2022/01/05 08:00 | Dusan Obradovic v Victorio Marquiselli | 6-2,6-1 |
| ITF M15 Monastir | 2021/12/30 12:55 | Riccardo Balzerani v Dusan Obradovic | 7-5,6-3 |
| ITF M15 Monastir | 2021/12/28 09:35 | Thomas Deschamps v Dusan Obradovic | 3-6,2-6 |
| ITF M15 Monastir | 2021/12/22 10:10 | Dusan Obradovic v Moez Echargui | 1-6,3-6 |
| ITF M15 Pirot | 2021/09/20 08:00 | Dusan Obradovic v Luca Castagnola | 3-6,5-7 |
| ITF M15 Oberhaching | 2022/02/13 08:00 | Paul Woerner v Simon Freund | 2-6,6-7 |
| ATP Stockholm | 2021/11/06 11:00 | Simon Freund v Nino Serdarusic | 1-6,7-6,3-6 |
| ITF M15 Doha | 2021/10/22 12:30 | Simon Freund v Julian Cash | 5-7,3-6 |
| ITF M15 Doha | 2021/10/21 12:30 | Simon Freund v Joshua Paris | 6-1,7-6 |
| ITF M15 Doha | 2021/10/20 12:30 | Simon Freund v Christoffer Solberg | 6-3,6-4 |
| ITF M25 Falun | 2021/09/28 10:55 | Maximilian Neuchrist v Simon Freund | 4-6,6-3,6-2 |
| ITF M25 Falun | 2021/09/27 09:45 | Simon Freund v Robin Thour | 4-6,6-3,12-10 |
| ITF M25 Jonkoping | 2021/09/21 09:10 | Jonathan Mridha v Simon Freund | 7-5,4-6,7-5 |