Stadium: Court 5 Round: 45 Ground: Clay
| Challenger Charlottesville Qual | 2016/10/30 16:00 | Jarryd Chaplin v Gonzales Austin | 2-6,1-6 |
| Challenger Charlottesville Qual | 2016/10/29 16:00 | Ammar Faleh Alhogbani v Jarryd Chaplin | 6-7,4-6 |
| Challenger Kaohsiung Qual | 2016/09/17 03:10 | Yasutaka Uchiyama v Jarryd Chaplin | 6-3,7-6 |
| Challenger Shanghai Qual | 2016/09/04 03:20 | Jarryd Chaplin v Sergey Betov | 5-7,4-6 |
| Challenger Winnipeg Qual | 2016/07/09 17:00 | Joshua Peck v Jarryd Chaplin | 3-6,6-1,6-3 |
| ITF Canada F4 | 2016/06/29 20:00 | Jarryd Chaplin v Joshua Peck | 6-7,6-7 |
| ITF Canada F3 | 2016/06/22 17:00 | Jarryd Chaplin v Henry Choi | 6-7,6-7 |
| ITF Israel F10 | 2016/06/10 07:00 | Jarryd Chaplin v Nick Chappell | 7-5,3-6,2-6 |
| ITF South Africa F3 Qual | 2016/11/11 23:00 | Curtis Clarke v Mark Oljaca | 6-2,6-2 |
| ITF South Africa F2 Qual | 2016/11/05 23:00 | Vasilios Caripi v Mark Oljaca | 7-5,6-2 |
| ITF South Africa F2 Qual | 2016/11/04 23:00 | Matt Seeberger v Mark Oljaca | 6-7,6-1,4-6 |
| ITF South Africa F1 | 2016/10/31 23:00 | Johannes Myburgh v Mark Oljaca | 6-2,1-6,6-2 |
| ITF USA F31 Qual | 2016/10/08 14:00 | Guanarteme N Delgado v Mark Oljaca | 6-4,6-0 |
| ITF Canada F9 Qual | 2016/09/17 16:00 | Washi Gervais v Mark Oljaca | 6-2,6-1 |
| ITF Guam F1 | 2016/05/24 06:30 | Mark Oljaca v Takuto Niki | 4-6,0-6 |
| Challenger Bordeaux Qual | 2016/05/07 08:00 | Mark Oljaca v Maxime Hamou | 2-6,2-6 |