Round: 44 Ground: Hardcourt outdoor
| ITF USA F12 Qual | 2016/04/04 14:00 | Jarryd Chaplin v Dane Webb | 4-6,4-6 |
| Challenger Drummondville Qual | 2016/03/13 15:20 | Hugo Nys v Jarryd Chaplin | 6-2,6-2 |
| Challenger Drummondville Qual | 2016/03/12 18:00 | Jarryd Chaplin v Nicaise Muamba | 1-6,7-5,6-4 |
| ITF Canada F1 | 2016/03/01 16:30 | Alejandro Tabilo v Jarryd Chaplin | 6-3,3-6,7-6 |
| ITF Canada F1 Qual | 2016/02/28 15:00 | Jarryd Chaplin v Benjamin Sigouin | 7-6,3-6,7-6 |
| Challenger - Launceston | 2016/02/03 04:30 | Jarryd Chaplin v Benjamin Mitchell | 4-6,2-6 |
| Challenger - Launceston | 2016/02/01 02:20 | Jarryd Chaplin v Alexei Popyrin | 6-2,7-5 |
| ITF Kuwait F1 | 2016/01/10 23:00 | Yoshihito Nishioka v Jarryd Chaplin | 3-6,6-1,6-4 |
| ITF Israel F8 Qual | 2016/05/22 06:30 | Jordan Hasson v Shahar Elbaz | 1-6,2-6 |
| ITF Israel F7 | 2016/05/14 11:30 | Maciej Smola v Jordan Hasson | 6-3,7-5 |
| ITF Israel F6 | 2016/03/20 08:30 | Jordan Hasson v Shahar Elbaz | 3-6,6-3,3-6 |
| ITF Israel F5 | 2016/03/12 09:00 | Jordan Hasson v Alexander Centenari | 5-7,5-7 |
| ITF Israel F4 | 2016/03/06 09:30 | Yannai Barkai v Jordan Hasson | 6-2,3-6,6-1 |
| ITF Israel F3 MD | 2016/02/21 07:30 | Alon Elia v Jordan Hasson | 6-2,6-2 |
| ITF Israel F3 MD | 2016/02/20 12:30 | Jordan Hasson v Edan Bakshi | 6-4,6-3 |
| ITF Israel F2 | 2016/02/13 10:30 | Lucas Catarina v Jordan Hasson | 6-1,6-0 |