Stadium: Casper Court Round: 44 Ground: Clay
| ITF - M25 Naples | 2020/02/10 16:00 | Daniel Dutra Da Silva v Ignat, Dragos Constantin | 6-2,7-5 |
| ITF - M25 Naples | 2020/02/09 15:00 | Daniel Dutra Da Silva v Bradley, Julian | 6-0,7-5 |
| Palm Coast, Singles M-ITF-USA-05A | 2020/02/08 17:35 | Alexander Ritschard v Daniel Dutra Da Silva | 2-6,6-1,6-2 |
| Palm Coast, Singles M-ITF-USA-05A | 2020/02/07 17:30 | Torebko, Peter v Daniel Dutra Da Silva | 6-2,6-7,6-7 |
| Palm Coast, Singles M-ITF-USA-05A | 2020/02/06 15:00 | Daniel Dutra Da Silva v Lindell, Christian | 7-6,7-5 |
| Palm Coast, Singles M-ITF-USA-05A | 2020/02/05 16:35 | Daniel Dutra Da Silva v Slobodchikov, Ronald | 7-6,6-1 |
| Palm Coast, Singles M-ITF-USA-05A | 2020/02/04 16:20 | Daniel Dutra Da Silva v Guy Orly Iradukunda | 6-2,6-1 |
| Palm Coast, Singles M-ITF-USA-05A | 2020/02/03 15:00 | Daniel Dutra Da Silva v Giddens, Maxwell | 6-3,6-2 |
| ITF - M25 Naples | 2020/02/10 15:30 | Bendeck, Jose Daniel v Witten, Jesse | 2-6,5-7 |
| ITF - M25 Naples | 2020/02/09 15:00 | Witten, Jesse v Simon Freund | 7-6,6-4 |
| ITF M15 Cancun | 2020/01/30 18:10 | Chad Kissell v Witten, Jesse | 3-6,6-2,7-6 |
| ITF M15 Cancun | 2020/01/29 15:50 | Jose Pereira v Witten, Jesse | 1-6,1-6 |
| ITF M15 Cancun | 2020/01/28 15:00 | Witten, Jesse v Wettengel, Chris | 6-3,6-1 |
| ITF M15 Cancun | 2020/01/27 14:00 | Ribeiro Marcondes, Igor v Witten, Jesse | 6-3,3-6,9-11 |
| ITF M15 Cancun | 2020/01/26 19:00 | Witten, Jesse v Patricio Alvarado | 6-3,6-3 |
| ITF - M25 Naples | 2019/11/19 18:55 | Witten, Jesse v Genaro Alberto Olivieri | 3-6,6-2,1-6 |