Round: 27 Ground: Hardcourt outdoor
| ITF Israel F9 | 2016/06/01 07:00 | Chaplin, Jarryd v Goldengoren, Tal | 6-3,3-6,6-3 |
| ITF Israel F9 | 2016/05/31 06:00 | Chaplin, Jarryd v Elia, Alon | 6-2,7-6 |
| ITF Israel F9 | 2016/05/29 07:00 | Chaplin, Jarryd v Switzler, Brant Vaughan | 6-3,6-2 |
| ITF Israel F9 | 2016/05/29 06:00 | Chaplin, Jarryd v Hasson, Jordan | 6-3,6-1 |
| ITF USA F12 Qual | 2016/04/04 14:00 | Chaplin, Jarryd v Webb, Dane | 4-6,4-6 |
| Challenger Drummondville Qual | 2016/03/13 15:20 | Hugo Nys v Chaplin, Jarryd | 6-2,6-2 |
| Challenger Drummondville Qual | 2016/03/12 18:00 | Chaplin, Jarryd v Nicaise Muamba | 1-6,7-5,6-4 |
| ITF Canada F1 | 2016/03/01 16:30 | Alejandro Tabilo v Chaplin, Jarryd | 6-3,3-6,7-6 |
| ITF Israel F9 | 2016/06/02 07:00 | Barkai, Yannai v Edan Leshem | 0-6,3-6 |
| ITF Israel F9 | 2016/05/31 06:00 | Johns, Collin v Edan Leshem | 4-6,4-6 |
| ITF Israel F8 | 2016/05/25 08:10 | Edan Leshem v Vega, Quinton | 2-6,6-7 |
| ITF Israel F8 | 2016/05/24 07:00 | Edan Leshem v Kapach, Ram | 6-2,6-3 |
| ITF Israel F7 | 2016/05/21 09:45 | Meister, Nicolas v Edan Leshem | 7-6,7-5 |
| ITF Israel F7 | 2016/05/20 09:20 | Edan Leshem v Dubail, Julien | 6-3,6-3 |
| ITF Israel F7 | 2016/05/19 09:55 | Schmid, Michal v Edan Leshem | 4-6,2-6 |
| ITF Israel F7 | 2016/05/18 08:20 | Voljacques, Hugo v Edan Leshem | 2-6,2-6 |