Stadium: COURT 6 Round: 46 Ground: Hardcourt outdoor
| Challenger Biella | 2016/07/26 16:00 | Matteo Donati v Hans Podlipnik-Castillo | 6-3,6-4 |
| Challenger Cali 2 | 2016/07/06 17:50 | Joao Souza v Hans Podlipnik-Castillo | 6-2,6-2 |
| Wimbledon Qual | 2016/06/20 16:20 | Hans Podlipnik-Castillo v Quentin Halys | 0-6,1-6 |
| Challenger Poprad Tatry | 2016/06/14 08:00 | Andre Ghem v Hans Podlipnik-Castillo | 6-3,6-3 |
| French Open Qual | 2016/05/18 08:00 | Hans Podlipnik-Castillo v Adam Pavlasek | 2-6,2-6 |
| French Open Qual | 2016/05/16 11:50 | Hans Podlipnik-Castillo v Miljan Zekic | 6-4,3-6,6-3 |
| Challenger Heilbronn Qual | 2016/05/07 12:35 | Andreas Beck v Hans Podlipnik-Castillo | 6-3,6-2 |
| Challenger Ostrava | 2016/04/26 12:15 | Janko Tipsarevic v Hans Podlipnik-Castillo | 7-6,3-6,6-4 |
| Challenger Fairfield Qual | 2016/10/08 21:30 | Connor Farren v Greg Jones | 6-7,3-6 |
| Challenger Stockton Qual | 2016/10/02 18:20 | Greg Jones v Emilio Gomez | 3-6,3-6 |
| Challenger Tiburon Qual | 2016/09/25 19:55 | Greg Jones v Dennis Nevolo | 6-7,1-6 |
| Challenger Tiburon Qual | 2016/09/24 18:40 | Lorenzo Sonego v Greg Jones | 2-6,7-6,4-6 |
| Challenger Granby Qual | 2016/07/31 16:30 | Greg Jones v Erik Crepaldi | 6-2,4-6,5-7 |
| Challenger Granby Qual | 2016/07/30 18:15 | Greg Jones v Luis David Martinez | 6-3,6-1 |
| ITF Canada F4 | 2016/06/29 19:35 | Greg Jones v Peter Polansky | 3-6,0-6 |
| ITF Canada F3 | 2016/06/21 17:00 | Alexis Galarneau v Greg Jones | 6-4,3-6,6-3 |