Round: 62 Ground: Hardcourt indoor
| ITF Cyprus F2 | 2016/11/23 07:30 | Vasile Antonescu v Luke Simkiss | 6-2,6-1 |
| ITF Cyprus F2 Qual | 2016/11/21 08:00 | Benjamin Pietri v Luke Simkiss | 3-6,4-6 |
| ITF Cyprus F2 Qual | 2016/11/20 11:00 | Luke Simkiss v Aliaksandr Prudnikau | 7-5,6-4 |
| ITF Cyprus F1 Qual | 2016/11/13 11:30 | Antoine Walch v Luke Simkiss | 6-2,7-6 |
| ITF Turkey F24 Qual | 2016/06/11 11:30 | Luke Simkiss v Shota Meparidze | 2-6,4-6 |
| ITF Turkey F23 MD | 2016/06/04 12:30 | Luke Simkiss v Bastien Kolly | 7-6,3-6,4-6 |
| ITF Spain F9 Qual | 2016/04/08 09:00 | Luke Simkiss v Maxim Tybar | 4-6,6-4,4-6 |
| ITF Tunisia F12 | 2016/03/26 08:30 | Alexander Thomas Grabher v Luke Simkiss | 7-5,6-3 |
| Challenger Columbus 2 Qual | 2016/11/20 17:05 | Gonzales Austin v Ruan Roelofse | 4-6,7-6,6-3 |
| Challenger Columbus 2 Qual | 2016/11/19 16:20 | Ruan Roelofse v Trey Yates | 6-4,6-7,7-6 |
| Challenger Champaign Qual | 2016/11/14 16:00 | Bradley Klahn v Ruan Roelofse | 6-3,6-2 |
| Challenger Champaign Qual | 2016/11/13 16:00 | Ruan Roelofse v Dominik Koepfer | 6-2,6-3 |
| Challenger Champaign Qual | 2016/11/12 17:05 | Evan Zhu v Ruan Roelofse | 4-6,4-6 |
| ITF USA F34 | 2016/10/27 18:25 | Rubin Statham v Ruan Roelofse | 6-3,6-2 |
| ITF USA F34 | 2016/10/23 20:10 | Ruan Roelofse v Brandon Nakashima | 6-3,6-0 |
| ITF USA F34 | 2016/10/22 20:00 | Sameer Kumar v Ruan Roelofse | 4-6,6-3,3-6 |