Round: 62 Ground: Clay
| ITF USA F17 Qual | 2016/06/05 14:00 | Justin Roberts v Drew Van Orderlain | 6-3,7-6 |
| ITF USA F19 | 2016/06/16 15:00 | Justin Roberts v Hans Hach Verdugo | 2-6,6-4,3-6 |
| ITF USA F19 Qual | 2016/06/13 15:00 | Justin Roberts v Ryoto Tachi | 6-1,6-2 |
| ITF USA F19 Qual | 2016/06/12 16:30 | Justin Roberts v Sahil Gaware | 6-4,6-2 |
| ITF USA F17 | 2016/06/08 14:55 | Takanyi Garanganga v Justin Roberts | 6-4,6-2 |
| ITF USA F17 Qual | 2016/06/06 14:35 | Justin Roberts v Christian Langmo | 6-4,4-6,7-5 |
| ITF USA F17 Qual | 2016/06/05 14:00 | Justin Roberts v Drew Van Orderlain | 6-3,7-6 |
| ITF Dominican Republic F3 | 2015/12/17 14:00 | Jaume Pla Malfeito v Justin Roberts | 6-7,7-5,6-1 |
| ITF Dominican Republic F3 | 2015/12/15 15:40 | Peter Bertran v Justin Roberts | 1-6,3-6 |
| ITF USA F20 Qual | 2016/06/18 19:30 | Drew Van Orderlain v Daniel Fainblum | 3-6,7-5,6-1 |
| ITF USA F18 | 2016/06/12 13:00 | Ezekiel Clark v Drew Van Orderlain | 6-2,6-2 |
| ITF USA F17 Qual | 2016/06/05 14:00 | Justin Roberts v Drew Van Orderlain | 6-3,7-6 |
| ITF USA F17 Qual | 2016/06/04 15:30 | Stefan Frljanic v Drew Van Orderlain | 4-6,6-7 |
| ITF Mexico F3 | 2016/05/15 15:00 | Junior Alexander Ore v Drew Van Orderlain | 6-4,6-4 |
| ITF USA F15 Qual | 2016/04/24 17:30 | Jonathan Chang v Drew Van Orderlain | 6-3,6-4 |
| ITF USA F15 Qual | 2016/04/22 21:30 | Drew Van Orderlain v Nicholas Reyes | 7-5,3-6,6-2 |
| ITF Turkey F15 | 2016/04/09 11:00 | Drew Van Orderlain v Rio Noguchi | 3-6,1-6 |