Cancoil Benfica's playoff games
| Game | Date ↑ | Time | Field | Home | Visitors | |
|---|---|---|---|---|---|---|
| C57 | Mon, Aug-27 | 6:00 pm | Barr Homes 3 | Valhalla II | 6 - 2 | Progress Physio |
| C60 | Mon, Aug-27 | 6:00 pm | Barr Homes 2 | Cancoil Benfica | 2 - 1 | Cataraqui III |
| D45 | Mon, Aug-27 | 6:00 pm | Barr Homes 4 | JKL Rangers | 0 - 3 | AIC |
| C58 | Mon, Aug-27 | 6:15 pm | John Machin Turf | Remax United | 3 - 0 | Jimmy's Sports Lounge SC |
| D43 | Mon, Aug-27 | 6:15 pm | CaraCo Home Field | First Responders FC | 4 - 1 | Red House FC |
| C59 | Mon, Aug-27 | 8:15 pm | John Machin Turf | Glasgow SC | 2 - 0 | WTC Red House |
| D44 | Mon, Aug-27 | 8:15 pm | CaraCo Home Field | Cotswold Home Inspection | 2 - 2 | King's Crew FC |
| Penalty Kicks | (4 - 3) | |||||
| B58 | Tue, Aug-28 | 6:00 pm | Barr Homes 3 | Valhalla | 7 - 1 | FC Legacy |
| B59* | Tue, Aug-28 | 6:30 pm | Woodbine 5 | Cataraqui II | 7 - 1 | Grizzly's |
| B57 | Tue, Aug-28 | 8:15 pm | CaraCo Home Field | The Keg FC | 4 - 1 | Pita Pit Empire Court |
| B60 | Tue, Aug-28 | 8:15 pm | Woodbine 5 | CFB Kingston | 1 - 5 | Paradiso Pizza |
| A44 | Wed, Aug-29 | 6:00 pm | Barr Homes 3 | Portuguese Benfica | 2 - 2 | Glenhaven United |
| Penalty Kicks | (4 - 5) | |||||
| A45 | Wed, Aug-29 | 6:00 pm | Barr Homes 4 | Portsmouth Celtic FC | 1 - 3 | Kingston Hot Fire |
| A43 | Wed, Aug-29 | 6:15 pm | John Machin Turf | Boca Nooners | 3 - 0 | Kingston Blues FC |
| D46 | Fri, Aug-31 | 6:00 pm | Barr Homes 2 | Independent FC | 3 - 0 | AIC |
| A46 | Fri, Aug-31 | 6:15 pm | CaraCo Home Field | Limestone City FC | 2 - 0 | Glenhaven United |
| B61 (f) | Fri, Aug-31 | 6:15 pm | Woodbine 5 | The Keg FC | 3 - 0 | Paradiso Pizza |
| C61 | Fri, Aug-31 | 6:15 pm | W J Henderson | Valhalla II | 0 - 1 | Cancoil Benfica |
| D47* | Fri, Aug-31 | 6:15 pm | Woodbine 5 | First Responders FC | 1 - 2 | Cotswold Home Inspection |
| A47 | Fri, Aug-31 | 8:15 pm | CaraCo Home Field | Boca Nooners | 0 - 2 | Kingston Hot Fire |
| B62 | Fri, Aug-31 | 8:15 pm | Woodbine 5 | Valhalla | 0 - 3 | Cataraqui II |
| C62 | Fri, Aug-31 | 8:15 pm | W J Henderson | Remax United | 2 - 0 | Glasgow SC |
| D48 | Sun, Sep-02 | 12:00 pm | Barr Homes 3 | Independent FC | 3 - 3 | Cotswold Home Inspection |
| Penalty Kicks | (4 - 3) | |||||
| C63 | Sun, Sep-02 | 1:30 pm | Barr Homes 2 | Remax United | 0 - 1 | Cancoil Benfica |
| B63 | Sun, Sep-02 | 2:30 pm | Barr Homes 4 | The Keg FC | 1 - 4 | Cataraqui II |
| A48 | Sun, Sep-02 | 4:00 pm | Barr Homes 3 | Limestone City FC | 5 - 2 | Kingston Hot Fire |