Round: 44 Ground: Hardcourt outdoor
| ITF Canada F7 Qual | 2016/09/04 13:00 | Drew Van Orderlain v Gervais, Washi | 6-7,3-6 |
| USA F26, Singles Qualifying | 2016/07/30 15:30 | Donaldson, Brandon v Drew Van Orderlain | 6-2,6-3 |
| ITF Canada F5 Qual | 2016/07/02 17:00 | Drew Van Orderlain v Maginley, J. | 2-6,3-6 |
| ITF USA F22 Qual | 2016/06/26 14:00 | Drew Van Orderlain v Colin Markes | 3-6,4-6 |
| ITF USA F22 Qual | 2016/06/25 17:00 | Drew Van Orderlain v van Meter, Joseph W | 6-4,6-3 |
| ITF USA F20 Qual | 2016/06/19 17:00 | Justin Roberts v Drew Van Orderlain | 7-6,6-3 |
| ITF USA F20 Qual | 2016/06/18 19:30 | Drew Van Orderlain v Fainblum, Daniel | 3-6,7-5,6-1 |
| ITF USA F18 | 2016/06/12 13:00 | Ezekiel Clark v Drew Van Orderlain | 6-2,6-2 |