Stadium: Court 4 Round: 27 Ground: Hardcourt outdoor
| ITF M15 Sao Bras Alportel | 2019/09/05 09:00 | Marek Gengel v Simon Freund | 2-6,1-6 |
| ITF M15 Sao Bras Alportel | 2019/09/03 10:00 | Tomas Luis v Simon Freund | 1-6,1-6 |
| ITF M15 Ystad | 2019/08/07 08:15 | Simon Freund v Juan Manuel Cerundolo | 2-6,6-7 |
| ITF M15 Pittsburgh | 2019/07/07 15:00 | Alexander Cozbinov v Simon Freund | 2-6,6-2,6-1 |
| ITF M15 Pittsburgh | 2019/07/06 17:00 | Paul Oosterbaan v Simon Freund | 1-6,1-6 |
| ITF M15 Pittsburgh | 2019/07/04 15:25 | Simon Freund v Ricardo Rodriguez-Pace | 3-6,6-1,7-5 |
| ITF M15 Pittsburgh | 2019/07/02 14:00 | John Harrison Richmond v Simon Freund | 4-6,3-6 |
| ITF M15 Rochester | 2019/06/29 19:00 | Simon Freund v Strong Kirchheimer | 1-6,5-7 |
| ITF M15 Sao Bras Alportel | 2019/09/05 10:35 | Anton Matusevich v Patrik Niklas-Salminen | 6-4,6-2 |
| ITF M15 Sao Bras Alportel | 2019/09/04 11:15 | Anton Matusevich v Goncalo Falcao | 6-3,6-3 |
| ITF M15 Piombino | 2019/08/31 17:30 | Hugo Gaston v Anton Matusevich | 3-6,7-6,7-5 |
| ITF M15 Piombino | 2019/08/30 19:00 | Anton Matusevich v Yannick Mertens | 6-3,6-2 |
| ITF M15 Piombino | 2019/08/29 12:45 | Evan Furness v Anton Matusevich | 2-6,6-4,6-7 |
| ITF M15 Piombino | 2019/08/27 13:20 | Anton Matusevich v Moritz Trocker | 6-1,6-1 |
| ITF M25 Chiswick | 2019/08/10 12:30 | Anton Matusevich v Igor Sijsling | 6-4,1-6,4-6 |
| ITF M25 Chiswick | 2019/08/09 10:30 | Anton Matusevich v Julian Ocleppo | 6-4,6-2 |