| ITF Dominican Republic F1 | 11/25 14:00 | 62 | Simon Freund v Anshumat Srivastava | 6-0,6-3 | |
| ITF Dominican Republic F1 | 11/24 13:30 | 62 | Simon Freund v Arsav Mohanty | 6-4,6-1 | |
| ITF Sweden F4 | 09/23 11:45 | 54 | Marius Ruzgas v Simon Freund | 6-3,7-6 | |
| ITF Sweden F4 | 09/22 14:50 | 54 | Simon Freund v Pak Long Yeung | 7-6,7-6 | |
| Challenger Bastad Qual | 07/07 09:20 | 45 | Simon Freund v Dante Gennaro | 2-6,4-6 | |
| ITF USA F31 | 09/16 17:15 | 60 | Samuel Shropshire v Simon Freund | 6-2,6-2 | |
| ITF USA F29 | 09/17 17:00 | 60 | Jarryd Woog v Simon Freund | 6-3,6-3 | |
| ITF USA F29 | 09/16 17:00 | 60 | Simon Freund v Shane Vinsant | 7-6,6-4 |