Stadium: Court 2 Round: 44 Ground: Clay
| ITF M15 Cancun | 2020/01/30 18:10 | Chad Kissell v Jesse Witten | 3-6,6-2,7-6 |
| ITF M15 Cancun | 2020/01/29 15:50 | Jose Pereira v Jesse Witten | 1-6,1-6 |
| ITF M15 Cancun | 2020/01/28 15:00 | Jesse Witten v Chris Wettengel | 6-3,6-1 |
| ITF M15 Cancun | 2020/01/27 14:00 | Igor Marcondes v Jesse Witten | 6-3,3-6,9-11 |
| ITF M15 Cancun | 2020/01/26 19:00 | Jesse Witten v Patricio Alvarado | 6-3,6-3 |
| ITF M25 Naples | 2019/11/19 18:55 | Jesse Witten v Genaro Alberto Olivieri | 3-6,6-2,1-6 |
| ITF M25 Naples | 2019/10/30 14:00 | Jose Olivares v Jesse Witten | 5-7,6-7 |
| ITF M25 Naples | 2019/10/29 14:00 | Jesse Witten v Vladislav Melnic | 6-4,4-6,10-3 |
| ITF M25 Palm Coast | 2020/02/03 15:00 | Toby Alex Kodat v Simon Freund | 6-3,6-2 |
| ITF M25 Rancho Santa Fe | 2020/01/13 18:00 | Riley Smith v Simon Freund | 6-3,7-6 |
| ITF M25 Los Angeles | 2020/01/09 19:10 | Simon Freund v Christian Lindell | 3-6,4-6 |
| ITF M25 Los Angeles | 2020/01/08 20:00 | Keegan Smith v Simon Freund | 7-6,4-6,1-6 |
| ITF M25 Los Angeles | 2020/01/07 19:45 | Simon Freund v Tanner K Smith | 6-3,6-3 |
| ITF M25 Los Angeles | 2020/01/06 18:00 | Simon Freund v Errol Smith | 6-4,6-7,11-9 |
| ITF M15 Doha | 2019/12/19 11:40 | Simon Freund v Harry Wendelken | 0-6,2-6 |
| ITF M15 Doha | 2019/12/18 13:30 | Oleksii Krutykh v Simon Freund | 6-4,5-7,3-6 |