Round: 62 Ground: Hardcourt outdoor
| 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 Thailand F9 | 2015/12/02 04:15 | Jarryd Chaplin v Kento Takeuchi | 6-3,4-6,2-6 |
| ITF USA F12 Qual | 2016/04/03 13:00 | Dane Webb v Hunter Reese | 6-4,6-1 |
| ITF USA F12 Qual | 2016/04/02 14:00 | Dane Webb v Eric Rutledge | 6-1,6-2 |
| ITF USA F9 Qual | 2016/02/26 17:00 | Augusto Laranja v Dane Webb | 6-4,6-1 |
| ITF USA F8 Qual | 2016/02/21 17:00 | Dane Webb v Jorge Montero | 3-6,6-2,6-3 |
| ITF USA F8 Qual | 2016/02/20 16:30 | Sylvester Emmanuel v Dane Webb | 2-6,7-6,1-6 |
| ITF USA F8 Qual | 2016/02/19 16:30 | Dane Webb v Gonzalo Achondo | 7-5,7-5 |
| Challenger Dallas Qual | 2016/01/30 19:10 | Dane Webb v Maximiliano Estevez | 7-5,6-3 |
| ITF Dominican Republic F3 | 2015/12/14 13:30 | Dane Webb v Hunter Reese | 5-7,6-3,6-7 |