| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 06.07.2014 | Matchday 3 | Matchday 3 | H | ![]() | Brampton United | W | 4:1 |
| 20.07.2014 | Matchday 3 | Matchday 3 | H | ![]() | Serbian White Eagles | L | 0:1 |
| 27.07.2014 | Matchday 3 | Matchday 3 | A | ![]() | Niagara United | W | 4:0 |
| 03.08.2014 | Matchday 4 | Matchday 4 | H | ![]() | North York Astros | L | 1:2 |
| 16.08.2014 | Matchday 4 | Matchday 4 | A | ![]() | London City | D | 2:2 |
| 25.08.2014 | Matchday 4 | Matchday 4 | A | ![]() | Burlington SC | W | 4:0 |
| 31.08.2014 | Matchday 4 | Matchday 4 | H | ![]() | London City | L | 3:5 |
| 08.09.2014 | Matchday 5 | Matchday 5 | A | ![]() | SC Waterloo | L | 2:4 |
| 14.09.2014 | Matchday 5 | Matchday 5 | A | ![]() | Serbian White Eagles | W | 3:1 |
| 21.09.2014 | Matchday 5 | Matchday 5 | H | ![]() | Toronto Croatia | W | 5:4 |
| 28.09.2014 | Matchday 5 | Matchday 5 | H | ![]() | York Region Shooters | D | 2:2 |
| 05.10.2014 | Matchday 6 | Matchday 6 | A | ![]() | Brampton United | W | 1:0 |
| Date | Round | Round | H/A | Res. | |||
| 12.10.2014 | Quarter-finals | Quarter-Finals | H | ![]() | Serbian White Eagles | W | 3:0aet |
| 19.10.2014 | Semi-finals | Semi-Final | A | ![]() | Toronto Croatia | L | 1:2 |
Kingston FC









