Stadium: Court 7 Round: 45 Ground: Hardcourt indoor
| Challenger Kaohsiung Qual | 2016/09/17 03:10 | Yasutaka Uchiyama v Chaplin, Jarryd | 6-3,7-6 |
| Challenger Shanghai Qual | 2016/09/04 03:20 | Chaplin, Jarryd v Betov, Sergey | 5-7,4-6 |
| Challenger Winnipeg Qual | 2016/07/09 17:00 | Peck, Joshua v Chaplin, Jarryd | 3-6,6-1,6-3 |
| ITF Canada F4 | 2016/06/29 20:00 | Chaplin, Jarryd v Peck, Joshua | 6-7,6-7 |
| ITF Canada F3 | 2016/06/22 17:00 | Chaplin, Jarryd v Choi, Henry | 6-7,6-7 |
| ITF Israel F10 | 2016/06/10 07:00 | Chaplin, Jarryd v Nick Chappell | 7-5,3-6,2-6 |
| ITF Israel F10 | 2016/06/09 07:00 | Barry, Sam v Chaplin, Jarryd | 2-6,7-5,3-6 |
| ITF Israel F10 | 2016/06/08 06:30 | Ovil, Orel v Chaplin, Jarryd | 1-6,2-6 |