Round: 44 Ground: Hardcourt outdoor
| ITF Spain F33 | 2016/10/12 11:00 | Ricardo Ojeda Lara v Maciej Rajski | 6-3,6-3 |
| ITF Spain F33 | 2016/10/10 10:00 | Jaime Fermosell v Maciej Rajski | 6-7,6-7 |
| ITF Portugal F12 | 2016/10/06 12:25 | Andres Artunedo Martinavarr v Maciej Rajski | 7-5,4-6,7-6 |
| ITF Portugal F12 | 2016/10/05 14:25 | Fred Gil v Maciej Rajski | 6-3,3-6,4-6 |
| ITF Portugal F11 | 2016/09/30 10:00 | Maciej Rajski v Miguel Semedo | 3-6,7-5,4-6 |
| ITF Portugal F11 | 2016/09/29 09:30 | Maciej Rajski v Peter Bothwell | 6-4,6-2 |
| ITF Portugal F11 | 2016/09/28 09:30 | Yannick Jankovits v Maciej Rajski | 6-2,4-6,4-6 |
| ITF Portugal F11 Qual | 2016/09/26 12:00 | Maciej Rajski v Daniel Batista | 6-2,6-3 |
| ITF USA F39 Qual | 2016/11/28 17:32 | Jonathan Ho v Jimmy Bendeck | 7-5,3-6,4-5 |
| ITF USA F39 Qual | 2016/11/28 17:30 | Jonathan Ho v Jaime Bendeck | 7-5,3-6,4-6 |
| ITF USA F39 Qual | 2016/11/26 22:30 | Pirmin Haenle v Jonathan Ho | 2-6,5-7 |
| Challenger Columbus 2 Qual | 2016/11/19 18:00 | Jonathan Ho v Bradley Klahn | 2-6,2-6 |
| Challenger Knoxville Qual | 2016/11/06 15:00 | Ryan Shane v Jonathan Ho | 6-2,6-2 |
| Challenger Charlottesville Qual | 2016/10/30 14:00 | Yuki Bhambri v Jonathan Ho | 6-4,6-4 |
| ITF USA F32 Qual | 2016/10/17 17:05 | Jonathan Ho v John McNally | 3-6,7-6,4-6 |
| ITF USA F32 Qual | 2016/10/16 16:00 | Jonathan Ho v Jeremiah Gonzalez | 6-4,6-4 |