Stadium: COURT 2 Round: 46 Ground: Hardcourt outdoor
| Fairfield, USA, Qualifications | 2016/10/10 17:00 | Glasspool, Lloyd v Klein, Brydan | 4-6,3-6 |
| Fairfield, USA, Qualifications | 2016/10/09 18:20 | Glasspool, Lloyd v Crepaldi, Erik | 6-2,6-3 |
| Fairfield, USA, Qualifications | 2016/10/08 17:00 | Glasspool, Lloyd v Hendrik Jebens | 6-3,6-7,7-6 |
| Challenger Tiburon | 2016/09/27 19:35 | Joris De Loore v Glasspool, Lloyd | 6-2,7-6 |
| Challenger Tiburon Qual | 2016/09/26 17:00 | Nevolo, Dennis v Glasspool, Lloyd | 3-6,6-4,6-7 |
| Challenger Tiburon Qual | 2016/09/25 17:00 | Hubert Hurkacz v Glasspool, Lloyd | 7-5,2-6,5-7 |
| Challenger Tiburon Qual | 2016/09/24 20:35 | Nielsen, Frederik v Glasspool, Lloyd | 7-5,1-6,4-6 |
| Challenger Columbus | 2016/09/21 15:00 | Hubert Hurkacz v Glasspool, Lloyd | 6-4,7-5 |
| Challenger Las Vegas Qual | 2016/10/15 19:35 | Roelofse, Ruan v Cozbinov, Alexander | 6-2,6-2 |
| Fairfield, USA, Qualifications | 2016/10/10 17:00 | Podlipnik, Hans v Roelofse, Ruan | 7-5,1-6,6-3 |
| Fairfield, USA, Qualifications | 2016/10/09 19:10 | Roelofse, Ruan v Salvatore Caruso | 6-3,6-4 |
| Fairfield, USA, Qualifications | 2016/10/08 20:25 | Roelofse, Ruan v Collin Altamirano | 6-3,4-6,7-6 |
| Others | 2016/09/25 08:00 | Golubev, Andrey v Roelofse, Ruan | 3-6,7-6,7-6 |
| Others | 2016/09/24 10:30 | Roelofse, Ruan v Vasilevski, Andrei | 7-6,5-7,7-5 |
| Challenger Izmir Qual | 2016/09/17 11:45 | Marek Jaloviec v Roelofse, Ruan | 7-6,7-6 |
| Challenger Izmir Qual | 2016/09/17 09:00 | Roelofse, Ruan v O'Brien, Dean | 6-0,6-3 |