Round: 27 Ground: Hardcourt outdoor
| US Open Qual | 2016/08/25 19:20 | Matthew Barton v Jan Satral | 4-6,4-6 |
| US Open Qual | 2016/08/23 22:10 | Nikoloz Basilashvili v Matthew Barton | 7-6,2-6,6-7 |
| ATP Newport Qual | 2016/07/11 17:50 | Matthew Barton v Michal Przysiezny | 3-6,3-6 |
| ATP Newport Qual | 2016/07/10 18:00 | Matthew Barton v Adrien Bossel | 7-6,6-3 |
| Wimbledon | 2016/07/01 10:30 | John Isner v Matthew Barton | 7-6,7-6,7-6 |
| Wimbledon | 2016/06/28 14:10 | Albano Olivetti v Matthew Barton | 7-6,6-7,3-6,7-6,12-14 |
| Wimbledon Qual | 2016/06/24 14:40 | Karen Khachanov v Matthew Barton | 6-7,7-6,2-6,3-6 |
| Wimbledon Qual | 2016/06/22 10:00 | Marcelo Arevalo v Matthew Barton | 3-6,4-6 |
| Challenger Aptos | 2016/08/09 18:00 | Dayne Kelly v Benjamin Mitchell | 3-6,1-6 |
| Challenger Granby Qual | 2016/07/31 16:30 | Dayne Kelly v Raymond Sarmiento | 4-6,4-6 |
| ITF USA F24 | 2016/07/20 18:20 | Dayne Kelly v Alfredo Perez | 6-2,3-6,3-6 |
| Challenger Winnipeg | 2016/07/14 16:50 | Dayne Kelly v Yoshihito Nishioka | 3-6,3-6 |
| Challenger Winnipeg | 2016/07/13 15:00 | Marinko Matosevic v Dayne Kelly | 7-6,6-7,3-6 |
| Challenger Winnipeg Qual | 2016/07/10 15:00 | Dayne Kelly v Joshua Peck | 7-6,6-3 |
| ITF USA F23 | 2016/06/28 14:00 | Dayne Kelly v Takanyi Garanganga | 4-6,4-6 |
| ITF Hong Kong F2 Qual | 2016/06/16 22:00 | Xin Gao v Dayne Kelly | 1-6,6-2,6-3 |