Round: 44 Ground: Hardcourt outdoor
| ITF Israel F9 | 2016/05/29 06:00 | Jarryd Chaplin v Jordan Hasson | 6-3,6-1 |
| 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 Israel F8 | 2016/05/24 12:40 | Daniel Tamir v Brant Vaughan Switzler | 6-4,6-4 |
| ITF Israel F8 Qual | 2016/05/23 06:00 | George Davies v Brant Vaughan Switzler | 6-7,2-6 |
| ITF USA F33 Qual | 2015/11/14 16:00 | Brant Vaughan Switzler v Henrik Wiersholm | 1-6,4-6 |
| ITF Canada F5 Qual | 2015/07/19 20:00 | Brant Vaughan Switzler v Riaan Du Toit | 3-6,2-6 |