Stadium: COURT 6 Round: 54 Ground: Hardcourt outdoor
| Challenger Fairfield Qual | 2016/10/09 19:05 | Hans Podlipnik-Castillo v Greg Jones | 6-4,3-6,6-3 |
| 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 Fairfield Qual | 2016/10/09 19:10 | Ruan Roelofse v Salvatore Caruso | 6-3,6-4 |
| Challenger Fairfield Qual | 2016/10/08 20:25 | Ruan Roelofse v Collin Altamirano | 6-3,4-6,7-6 |
| Others | 2016/09/25 08:00 | Andrey Golubev v Ruan Roelofse | 3-6,7-6,7-6 |
| Others | 2016/09/24 10:30 | Ruan Roelofse v Andrei Vasilevski | 7-6,5-7,7-5 |
| Challenger Izmir Qual | 2016/09/17 11:45 | Marek Jaloviec v Ruan Roelofse | 7-6,7-6 |
| Challenger Izmir Qual | 2016/09/17 09:00 | Ruan Roelofse v Dean O'Brien | 6-0,6-3 |
| Challenger Aptos Qual | 2016/08/07 18:30 | Raymond Sarmiento v Ruan Roelofse | 6-3,6-2 |
| Challenger Leon Qual | 2016/03/27 19:05 | Fabricio Neis v Ruan Roelofse | 6-3,6-2 |