Round: 45 Ground: Hardcourt outdoor
| ITF Canada F4 | 2016/06/29 17:00 | Michael Genender v Τζέισον Τζανγκ | 2-6,3-6 |
| ITF Canada F3 | 2016/06/23 17:00 | Michael Genender v Philip Bester | 1-6,0-6 |
| ITF Canada F3 | 2016/06/21 20:35 | Spencer Furman v Michael Genender | 3-6,3-6 |
| ITF Canada F3 Qual | 2016/06/20 17:00 | Jack Mingjie Lin v Michael Genender | 5-7,6-3,2-6 |
| ITF Canada F3 Qual | 2016/06/19 17:00 | Michael Genender v Jared Maclean | 6-1,6-2 |
| ITF USA F2 Qual | 2016/01/10 18:00 | Michael Genender v Τζέικομπ Μπρουμ | 6-2,6-4 |
| ITF USA F2 Qual | 2016/01/09 18:00 | Νέιθαν Πόνγουιθ v Michael Genender | 3-6,6-4,4-6 |
| ITF USA F1 Qual | 2016/01/04 17:00 | Nicholas S. Hu v Michael Genender | 6-4,3-6,6-2 |
| Challenger Dallas Qual | 2016/01/30 16:00 | Dean O'Brien v Clay Thompson | 4-6,2-6 |
| Τσάλεντζερ Κολόμπους | 2015/09/21 18:55 | Dean O'Brien v Σέκου Μπανγκουρά | 3-6,1-6 |
| Challenger Columbus Qual | 2015/09/20 16:10 | Dean O'Brien v Herkko Pollanen | 6-3,6-4 |
| ITF Uzbekistan F4 | 2015/06/10 06:25 | Temur Ismailov v Dean O'Brien | 6-2,6-1 |
| ITF Uzbekistan F4 | 2015/06/09 07:40 | Dean O'Brien v Pavel Tsoy | 6-3,6-4 |
| Challenger Drummondville Qual | 2015/03/16 15:45 | Άνταμ Ελ Μιχντάβι v Dean O'Brien | 6-3,6-2 |
| ITF Canada F2 Qual | 2015/03/08 18:00 | Dean O'Brien v Victor Krustev | 2-6,7-6,4-6 |
| ITF Canada F1 | 2015/03/04 16:20 | Dean O'Brien v Filip Veger | 2-6,2-6 |