Portuguese Benfica's playoff games
| Game | Date ↑ | Time | Field | Home | Visitors | |
|---|---|---|---|---|---|---|
| B57 | Tue, Aug-22 | 6:00 pm | Barr Homes 4 | Cataraqui II | 1 - 1 | Remax United |
| Penalty Kicks | (2 - 3) | |||||
| B60 | Tue, Aug-22 | 6:00 pm | Barr Homes 3 | Paradiso Pizza | 7 - 2 | Pita Pit Empire Court |
| B58 | Tue, Aug-22 | 8:15 pm | CaraCo Home Field | The Keg FC | 9 - 0 | FC Legacy |
| B59 | Tue, Aug-22 | 8:15 pm | Woodbine 5 | Valhalla | 6 - 1 | Grizzly's |
| A46 | Wed, Aug-23 | 6:00 pm | Barr Homes 4 | Limestone City FC | 5 - 2 | Glenhaven United |
| A47 | Wed, Aug-23 | 6:00 pm | Barr Homes 3 | Boca Nooners | 8 - 2 | Portsmouth Celtic FC |
| A48 | Fri, Aug-25 | 6:00 pm | Barr Homes 4 | Portuguese Benfica | 1 - 1 | Boca Nooners |
| Penalty Kicks | (5 - 4) | |||||
| A49 | Fri, Aug-25 | 6:00 pm | Barr Homes 3 | Kingston Hot Fire | 1 - 4 | Limestone City FC |
| B61 | Fri, Aug-25 | 6:15 pm | Woodbine 4 | The Keg FC | 4 - 1 | Remax United |
| B62 | Fri, Aug-25 | 8:15 pm | Woodbine 4 | Valhalla | 3 - 0 | Paradiso Pizza |
| B63 | Sun, Aug-27 | 1:00 pm | Barr Homes 4 | The Keg FC | 3 - 1 | Valhalla |
| A50 | Sun, Aug-27 | 3:00 pm | Barr Homes 3 | Portuguese Benfica | 3 - 3 | Limestone City FC |
| Penalty Kicks | (7 - 6) | |||||
| C57 | Mon, Sep-11 | 6:15 pm | Caton's 1 | CFB Kingston | 5 - 0 | JKL Rangers |
| C59 | Mon, Sep-11 | 6:15 pm | Woodbine 4 | Valhalla II | 1 - 3 | Progress Physio |
| D57 | Mon, Sep-11 | 6:15 pm | Woodbine 5 | Cataraqui III | 4 - 1 | King's Crew FC |
| D59 | Mon, Sep-11 | 6:15 pm | W J Henderson | AIC | 3 - 1 | Kingston Young Boys |
| C58 | Mon, Sep-11 | 8:15 pm | Caton's 1 | Cancoil Benfica | 2 - 1 | WTC Red House |
| C60 | Mon, Sep-11 | 8:15 pm | Woodbine 4 | Barr Homes FC | 2 - 1 | Glasgow SC |
| D58 | Mon, Sep-11 | 8:15 pm | Woodbine 5 | Cotswold Home Inspection | 0 - 0 | KTown FC |
| Penalty Kicks | (3 - 1) | |||||
| D60 | Mon, Sep-11 | 8:15 pm | W J Henderson | First Responders FC | 2 - 1 | Red House FC |
| C61 | Fri, Sep-15 | 6:15 pm | Woodbine 4 | CFB Kingston | 8 - 0 | Progress Physio |
| D61 | Fri, Sep-15 | 6:15 pm | W J Henderson | Cataraqui III | 3 - 0 | First Responders FC |
| C62 | Fri, Sep-15 | 8:15 pm | Woodbine 4 | Cancoil Benfica | 3 - 1 | Barr Homes FC |
| D62 | Fri, Sep-15 | 8:15 pm | W J Henderson | Cotswold Home Inspection | 2 - 5 | AIC |
| D63 | Sun, Sep-17 | 1:00 pm | Barr Homes 4 | Cataraqui III | 0 - 1 | AIC |
| C63 | Sun, Sep-17 | 3:00 pm | Barr Homes 3 | CFB Kingston | 0 - 2 | Cancoil Benfica |