Stadium: COURT 10 Round: 46 Ground: Hardcourt indoor
| Charlottesville, USA, Qualifying | 2016/10/29 16:00 | Ammar Faleh Alhogbani v Chaplin, Jarryd | 6-7,4-6 |
| 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 USA F32 | 2016/10/20 17:20 | Austin, Gonzales v Nuez Delgado, Guanarteme | 1-6,2-6 |
| ITF USA F32 | 2016/10/18 15:00 | Austin, Gonzales v Reese, Hunter | 7-6,6-3 |
| ITF USA F31 | 2016/10/13 17:50 | Bhambri, Yuki v Austin, Gonzales | 6-0,7-6 |
| ITF USA F31 | 2016/10/11 15:00 | Austin, Gonzales v Baughman, Deiton | 6-2,6-2 |
| Challenger Columbus | 2016/09/23 18:35 | Austin, Gonzales v Torpegaard, Mikael | 2-6,5-7 |
| Challenger Columbus | 2016/09/22 15:00 | Dancevic, Frank v Austin, Gonzales | 6-7,3-6 |
| Challenger Columbus | 2016/09/20 18:05 | Austin, Gonzales v Joyce, Martin | 6-4,6-2 |
| Columbus, USA, Qualifications | 2016/09/19 15:00 | Crepaldi, Erik v Austin, Gonzales | 2-6,2-6 |