Stadium: Court 2 Round: 44 Ground: Clay
| 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 Naples | 2019/10/28 14:00 | Martim L Prata v Jesse Witten | 4-6,7-5,10-12 |
| ITF M25 Naples | 2019/10/27 14:00 | Alexander Bernard v Jesse Witten | 4-6,2-6 |
| ITF M15 Cancun | 2019/09/23 16:00 | Jesse Witten v Rodrigo Banzer | 6-2,6-7,8-10 |
| ITF M15 Cancun | 2019/09/23 14:00 | Wulfrano M M Esdras v Jesse Witten | 2-6,1-6 |
| ITF M15 Cancun | 2019/09/22 18:30 | Michel-Alexandre Fortin v Jesse Witten | 3-6,1-6 |
| 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 |
| ITF M15 Doha | 2019/12/13 12:00 | Danylo Kalenichenko v Simon Freund | 7-6,6-2 |
| ITF M15 Doha | 2019/12/12 12:00 | Simon Freund v Aliaksandr Liaonenka | 6-1,6-0 |
| ITF M15 Doha | 2019/12/11 14:05 | Haadin Bava v Simon Freund | 2-6,1-6 |
| ITF M15 Meshref | 2019/11/15 08:00 | Simon Freund v Marko Tepavac | 4-6,2-6 |
| ITF M15 Meshref | 2019/11/14 07:55 | Simon Freund v Pak Long Yeung | 6-2,7-5 |