Stadium: Court 5 Round: 25 Ground: Clay
| ITF M15 Bratislava | 2021/08/25 11:35 | Simon Freund v Obrad Markovski | 6-3,6-4 |
| ITF M25 Kiseljak | 2022/06/01 09:35 | Frane Nincevic v Simon Freund | 6-7,6-2,7-6 |
| ITF M25 Kalmar | 2022/05/12 08:15 | Simon Freund v Karl Friberg | 1-6,1-6 |
| ITF M25 Kalmar | 2022/05/11 14:05 | Tom Gentzsch v Simon Freund | 6-7,4-6 |
| ITF M15 Monastir | 2022/05/05 08:30 | Simon Freund v Maxence Beauge | 4-6,1-6 |
| ITF M15 Monastir | 2022/05/04 08:30 | Timofey Stepanov v Simon Freund | 3-6,4-6 |
| ITF M15 Monastir | 2022/04/28 11:05 | Simon Freund v Omni Kumar | 7-6,3-6,5-7 |
| ITF M15 Monastir | 2022/04/26 08:30 | Viktor Jovic v Simon Freund | 6-7,0-6 |
| ITF M15 Sharm El Sheikh | 2022/03/23 07:30 | Simon Freund v Kirill Kivattsev | 3-6,5-7 |
| ITF M15 Ulcinj | 2022/05/25 08:00 | Lukas H Lilleengen v Obrad Markovski | 6-3,4-6,6-2 |
| ITF M15 Ulcinj | 2022/05/24 08:00 | Obrad Markovski v Matija Zugic | 6-4,4-6,10-6 |
| ITF M15 Ulcinj | 2022/05/23 08:00 | Obrad Markovski v Nikola Puric | 6-2,6-1 |
| ITF M15 Ulcinj | 2022/05/09 08:30 | Andre Biro v Obrad Markovski | 6-2,6-1 |
| ITF M25 Ulcinj | 2022/05/06 08:00 | Alex M Pujolras v Obrad Markovski | 6-2,6-2 |
| ITF M25 Ulcinj | 2022/05/05 10:40 | Obrad Markovski v Giovanni Mpetshi Perricard | 6-4,6-4 |
| ITF M25 Ulcinj | 2022/05/03 13:30 | Matija Samardzic v Obrad Markovski | 6-7,6-7 |
| ITF M25 Ulcinj | 2022/05/03 08:00 | Gal Emersic Potocnik v Obrad Markovski | 0-6,4-6 |