Stadium: Court 6 Round: 62 Ground: Hardcourt outdoor
| 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 |
| ITF M25 Ricany | 2021/09/01 11:40 | Antonin Bolardt v Simon Freund | 6-2,1-6,6-4 |
| ITF M15 Monastir | 2021/04/26 12:30 | Lorenzo Bresciani v Constantin Bittoun Kouzmine | 5-7,3-6 |
| ITF M15 Monastir | 2021/04/26 08:00 | Lorenzo Bresciani v Taketo Takamisawa | 5-7,6-4,10-1 |
| ITF M15 Monastir | 2021/04/25 09:00 | Andrea Guerrieri v Lorenzo Bresciani | 4-6,6-4,7-10 |
| ITF M15 Monastir | 2021/04/19 12:00 | Iiro Vasa v Lorenzo Bresciani | 7-6,1-6,10-7 |
| ITF M15 Monastir | 2021/04/18 13:00 | Lorenzo Bresciani v Marius Ruzgas | 7-6,6-3 |
| ITF M15 Monastir | 2021/04/12 08:00 | Lorenzo Bresciani v Sean Hodkin | 5-7,4-6 |
| ITF M15 Monastir | 2021/04/11 09:00 | Lorenzo Bresciani v Samir Hamza Reguig | 6-1,6-4 |
| ITF M15 Sharm El Sheikh | 2021/03/14 07:00 | Francesco Vilardo v Lorenzo Bresciani | 2-6,6-0,10-8 |