Calabria Italia's playoff games
| Game | Date ↑ | Time | Field | Home | Visitors | |
|---|---|---|---|---|---|---|
| PC1 | Fri, Sep-07 | 6:00 pm | Woodbine 2 | Valhalla | 5 - 1 | Portsmouth FC |
| PC2 | Fri, Sep-07 | 6:00 pm | Caton's 2 | Nooners | 6 - 2 | Rose & Crown LCFC III |
| PC3 | Fri, Sep-07 | 6:00 pm | Woodbine 5 | Gentry Homes Rangers | 1 - 2 | Brandees |
| PC4 | Fri, Sep-07 | 6:00 pm | Caton's 1 | Loyal Oarsman | 2 - 1 | Portuguese OT |
| PB1 | Sat, Sep-08 | 11:00 am | Caton's 2 | Cataraqui II | 2 - 0 | Cataraqui III |
| PB2* (f) | Sat, Sep-08 | 11:00 am | Woodbine 2 | The Keg FC | 3 - 0 | Soccer Post KUSC I |
| PB3 | Sat, Sep-08 | 1:00 pm | Caton's 2 | Kelsey's United | 5 - 2 | Philthy McNasty's |
| PB4 | Sat, Sep-08 | 1:00 pm | Woodbine 2 | Vita Inter SC | 1 - 4 | Grizzly's |
| PA1 | Sat, Sep-08 | 3:00 pm | Caton's 2 | Fever | 6 - 1 | El Salvador |
| PA2 | Sat, Sep-08 | 3:00 pm | Woodbine 2 | Soccer Post Inaria FC | 1 - 1 | Sleep Factory United |
| Penalty Kicks | (3 - 4) | |||||
| PA3 | Sat, Sep-08 | 5:00 pm | Caton's 2 | Sporting | 7 - 1 | Portuguese Benfica |
| PA4 | Sat, Sep-08 | 5:00 pm | Woodbine 2 | Pilot House LCFC I | 0 - 3 | Calabria Italia |
| PC5 | Sun, Sep-09 | 11:00 am | Woodbine 2 | Valhalla | 2 - 0 | Brandees |
| PC6 | Sun, Sep-09 | 11:00 am | Caton's 2 | Nooners | 4 - 1 | Loyal Oarsman |
| PB5 | Sun, Sep-09 | 1:00 pm | Woodbine 2 | Cataraqui II | 6 - 0 | Grizzly's |
| PB6 | Sun, Sep-09 | 1:00 pm | Caton's 2 | The Keg FC | 1 - 0 | Kelsey's United |
| PA5 | Sun, Sep-09 | 3:00 pm | Woodbine 2 | Fever | 3 - 1 | Sleep Factory United |
| PA6 | Sun, Sep-09 | 3:00 pm | Caton's 2 | Sporting | 2 - 4 | Calabria Italia |
| PC7 | Sun, Sep-16 | 11:00 am | Caton's 2 | Valhalla | 1 - 4 | Nooners |
| PB7 | Sun, Sep-16 | 1:00 pm | Caton's 2 | Cataraqui II | 1 - 1 | The Keg FC |
| Penalty Kicks | (4 - 5) | |||||
| PA7 | Sun, Sep-16 | 3:00 pm | Caton's 2 | Fever | 1 - 3 | Calabria Italia |