Stadium: Court 2 Round: 29 Ground: Hardcourt outdoor
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/07 11:15 | Gil, Fred v Johnson, Luke | 7-6,7-5 |
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/06 11:35 | Gil, Fred v David Poljak | 7-6,7-6 |
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/05 12:00 | Gil, Fred v Louis Tessa | 7-6,6-4 |
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/04 09:00 | Gil, Fred v Gabriele Moghini | 2-6,6-3,6-3 |
| Challenger Mallorca | 2019/08/26 15:00 | Gil, Fred v Viola, Matteo | 2-6,2-6 |
| ITF M15 Sintra | 2019/08/24 10:00 | Gil, Fred v Lucas Poullain | 2-6,1-6 |
| ITF M15 Sintra | 2019/08/23 14:35 | Gil, Fred v Cabral, Francisco | 6-1,6-4 |
| ITF M15 Sintra | 2019/08/22 15:25 | Gil, Fred v Faria, Luis | 6-3,6-1 |
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/07 09:30 | Simon Freund v Tverijonas, Julius | 6-2,6-0 |
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/06 09:00 | Simon Freund v Anton Matusevich | 7-5,6-4 |
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/05 09:00 | Marek Gengel v Simon Freund | 2-6,1-6 |
| Sao Bras Alportel, Singles Q M-ITF-POR-13A | 2019/09/03 10:00 | Tomas Luis v Simon Freund | 1-6,1-6 |
| Ystad, Singles M-ITF-SWE-03A | 2019/08/07 08:15 | Simon Freund v Juan Manuel Cerundolo | 2-6,6-7 |
| ITF M15 Pittsburgh | 2019/07/07 15:00 | Cozbinov, Alexander v Simon Freund | 2-6,6-2,6-1 |
| ITF M15 Pittsburgh | 2019/07/06 17:00 | C. Oosterbaan, Paul v Simon Freund | 1-6,1-6 |
| ITF M15 Pittsburgh | 2019/07/04 15:25 | Simon Freund v Rodriguez-Pace, Ricardo | 3-6,6-1,7-5 |