Stadium: Court 10 Round: 44 Ground: Hardcourt outdoor
| 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 Portoviejo | 2019/08/07 17:00 | Jorge Panta v Patricio Alvarado | 6-3,6-4 |
| ITF M25 Portoviejo | 2019/08/06 15:00 | Alexander Z Lapentti v Patricio Alvarado | 1-6,0-6 |
| ITF M25 Portoviejo | 2019/08/05 18:00 | Andres V Machuca v Patricio Alvarado | 0-6,1-6 |