Ground: Hardcourt indoor
| ITF Canada F9 Qual | 2014/09/08 14:00 | Du Toit, Riaan v Silverman, Cameron | 6-4,3-6,2-6 |
| ITF USA F22 | 2014/07/31 18:40 | Liam Broady v Silverman, Cameron | 6-1,3-6,6-1 |
| ITF USA F22 | 2014/07/30 17:15 | Webb, Dane v Silverman, Cameron | 3-6,1-6 |
| ITF USA F21 Qual | 2014/07/18 16:00 | Silverman, Cameron v Felix Corwin | 2-6,5-7 |
| ITF USA F20 | 2014/07/17 16:15 | Silverman, Cameron v Bambridge, Luke | 1-6,2-6 |
| ITF USA F20 | 2014/07/16 15:00 | Silverman, Cameron v Korinek, Andrew | 6-3,1-6,6-2 |
| ITF USA F19 | 2014/07/03 14:00 | Silverman, Cameron v Bambridge, Luke | 6-4,4-6,2-6 |
| ITF USA F19 | 2014/07/02 18:00 | Silverman, Cameron v Callahan, Hunter | 7-6,6-4 |
| ITF Canada F9 Qual | 2014/09/09 18:35 | Siller, Rogelio v Bester, Philip | 3-6,2-6 |
| ITF Canada F9 Qual | 2014/09/04 14:00 | Bester, Philip v Nguyen, Daniel | 6-2,6-7,3-6 |
| ITF Canada F9 Qual | 2014/09/03 16:20 | Bester, Philip v Koleganov, Egor | 6-3,6-4 |
| ITF Canada F9 Qual | 2014/09/02 14:00 | Bester, Philip v Wennakoski, Max | 6-3,6-4 |
| ITF Canada F8 | 2014/08/23 18:00 | Bester, Philip v Blake Mott | 7-6,6-7,3-6 |
| ITF Canada F8 | 2014/08/22 17:00 | Bester, Philip v Jones, Greg | 3-6,6-3,6-2 |
| Canada F7, Singles | 2014/08/15 23:45 | Omar Jasika v Bester, Philip | 4-6,7-6,6-4 |
| ITF Canada F4 | 2014/07/05 22:15 | Filip Peliwo v Bester, Philip | 6-4,6-4 |