Portuguese Benfica's playoff games
| Game | Date ↑ | Time | Field | Home | Visitors | |
|---|---|---|---|---|---|---|
| DP1 | Thu, Aug-26 | 8:30 pm | Woodbine 5 | LCFC III Fanatics | 0 - 0 | Brandees SC |
| Penalty Kicks | (3 - 2) | |||||
| DP2 | Thu, Aug-26 | 8:30 pm | Caton's 1 | Frontenac United | 3 - 1 | KPFC |
| BP1 (f) | Fri, Aug-27 | 6:00 pm | Caton's 2 | Da Boys FC | 3 - 0 | Brandees I |
| CP2 (f) | Fri, Aug-27 | 6:00 pm | Woodbine 2 | Loyal Oarsman | 3 - 0 | Portsmouth Celtic FC |
| BP2 | Fri, Aug-27 | 6:30 pm | Caton's 1 | Pilot House Nooners | 0 - 1 | Cataraqui II |
| CP3 | Fri, Aug-27 | 6:30 pm | Woodbine 5 | JKL Rangers | 2 - 1 | Kelsey's United |
| AP1 | Sun, Aug-29 | 6:00 pm | Woodbine 2 | AS Roma | 5 - 1 | Vita Inter SC |
| CP1* | Sun, Aug-29 | 6:00 pm | CFB | CFB Kingston | 0 - 7 | Cancoil Benfica |
| AP2 (f) | Sun, Aug-29 | 6:30 pm | Woodbine 4 | Portuguese Benfica | 3 - 0 | LCFC II |
| AP3 | Sun, Aug-29 | 6:30 pm | Woodbine 5 | Cataraqui I | 4 - 5 | Pilot House LCFC I |
| CP5 | Mon, Aug-30 | 6:00 pm | Caton's 2 | Loyal Oarsman | 3 - 1 | JKL Rangers |
| DP3 | Mon, Aug-30 | 6:00 pm | Woodbine 2 | Napanee FC | 0 - 1 | Frontenac United |
| DP4 | Mon, Aug-30 | 6:30 pm | Woodbine 5 | Sun Life FC | 1 - 0 | LCFC III Fanatics |
| CP4 | Mon, Aug-30 | 8:00 pm | Caton's 1 | Valhalla | 3 - 2 | Cancoil Benfica |
| AP4 | Tue, Aug-31 | 6:30 pm | Woodbine 5 | Soccer Plus FC | 2 - 2 | Pilot House LCFC I |
| Penalty Kicks | (3 - 4) | |||||
| BP3 | Tue, Aug-31 | 6:30 pm | Caton's 1 | Glenhaven United | 0 - 0 | Cataraqui II |
| Penalty Kicks | (0 - 3) | |||||
| AP5 | Tue, Aug-31 | 8:30 pm | Woodbine 5 | AS Roma | 1 - 1 | Portuguese Benfica |
| Penalty Kicks | (0 - 3) | |||||
| BP4 | Tue, Aug-31 | 8:30 pm | Caton's 1 | Ryatt United SC | 1 - 0 | Da Boys FC |
| DP5 | Wed, Sep-01 | 6:00 pm | Woodbine 2 | Sun Life FC | 1 - 0 | Frontenac United |
| CP6 | Wed, Sep-01 | 8:00 pm | Woodbine 5 | Valhalla | 2 - 1 | Loyal Oarsman |
| BP5 | Thu, Sep-02 | 6:00 pm | Woodbine 2 | Ryatt United SC | 0 - 1 | Cataraqui II |
| AP6 | Thu, Sep-02 | 6:30 pm | Woodbine 5 | Pilot House LCFC I | 0 - 2 | Portuguese Benfica |