Ground: Hardcourt outdoor
| ITF USA F21 Qual | 2014/07/21 15:00 | Yuanfeng Li v Jarryd Chaplin | 4-6,6-4,6-1 |
| ITF USA F21 Qual | 2014/07/20 15:30 | Henrik Wiersholm v Jarryd Chaplin | 5-7,5-7 |
| ITF USA F21 Qual | 2014/07/19 16:30 | Jarryd Chaplin v Vullnet Tashi | 7-6,6-3 |
| ITF Canada F6 Qual | 2014/07/14 17:00 | Farris Fathi Gosea v Jarryd Chaplin | 6-3,6-2 |
| ITF Canada F6 Qual | 2014/07/13 17:00 | Jarryd Chaplin v Ren Nakamura | 6-7,6-1,6-1 |
| ITF USA F14 | 2014/05/14 12:30 | Mitchell Krueger v Tom Fawcett | 2-6,7-6,6-2 |