Stadium: COURT 3 Round: 46 Ground: Hardcourt outdoor
| 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 Israel F10 | 2016/06/09 07:00 | Sam Barry v Jarryd Chaplin | 2-6,7-5,3-6 |
| ITF Israel F10 | 2016/06/08 06:30 | Orel Ovil v Jarryd Chaplin | 1-6,2-6 |
| ITF Israel F10 | 2016/06/07 09:30 | Motvey Radionov v Jarryd Chaplin | 1-6,4-6 |
| ITF Israel F9 | 2016/06/03 07:00 | Jarryd Chaplin v Edan Leshem | 4-6,1-6 |
| Challenger Bangkok 4 | 2016/08/30 09:50 | Edan Leshem v Sergey Betov | 6-3,3-6,6-1 |
| Challenger Bangkok 4 | 2016/08/28 07:00 | Sergey Betov v Chanon Phunsawat | 6-1,6-4 |
| Challenger Poznan | 2016/07/12 13:00 | Kimmer Coppejans v Sergey Betov | 6-3,6-1 |
| Challenger Poznan Qual | 2016/07/10 10:00 | Clement Geens v Sergey Betov | 6-3,6-0 |
| Challenger Poznan Qual | 2016/07/09 13:00 | Jan Zielinski v Sergey Betov | 6-4,3-6,4-6 |
| Challenger Marburg Qual | 2016/06/26 14:10 | Sergey Betov v Prajnesh Gunneswaran | 2-6,4-6 |
| Challenger Marburg Qual | 2016/06/26 08:00 | Peter Heller v Sergey Betov | 6-3,3-6,3-6 |
| Challenger Wroclaw Qual | 2016/02/14 12:40 | Sergey Betov v Vaclav Safranek | 4-6,4-6 |