All Competitions
| Game | Date ↑ | Time | Field | Home | Visitors | |
|---|---|---|---|---|---|---|
| A4 | Thu, May-13 | 6:30 pm | Caton's 1 | AS Roma | 1 - 0 | Portuguese Benfica |
| A8 | Wed, May-19 | 8:30 pm | Caton's 1 | Portuguese Benfica | 1 - 2 | The Keg FC |
| A16 | Wed, Jun-02 | 8:30 pm | Jim Beattie West | Portuguese Benfica | 2 - 2 | Clippers I |
| A12* | Fri, Jun-04 | 8:30 pm | Woodbine 5 | LCFC II | 0 - 5 | Portuguese Benfica |
| A22 | Wed, Jun-09 | 6:30 pm | Caton's 2 | Portuguese Benfica | 3 - 4 | Cataraqui I |
| A34 | Wed, Jun-23 | 6:30 pm | Caton's 2 | Portuguese Benfica | 2 - 0 | Joga Bonito |
| L10 | Fri, Jun-25 | 8:30 pm | Caton's 1 | Pilot House LCFC I | 4 - 3 | Portuguese Benfica |
| L21 | Fri, Jul-02 | 6:30 pm | Woodbine 2 | Portuguese Benfica | 2 - 0 | Cataraqui II |
| L24 | Tue, Jul-06 | 8:30 pm | Jim Beattie East | Portuguese Benfica | 6 - 0 | Pilot House Nooners |
| A28* | Mon, Jul-12 | 6:30 pm | Caton's 2 | Soccer Plus FC | 0 - 2 | Portuguese Benfica |
| L31* | Wed, Jul-14 | 8:30 pm | Woodbine 5 | Vita Inter SC | 2 - 1 | Portuguese Benfica |
| A40* | Tue, Jul-20 | 8:30 pm | Caton's 1 | Vita Inter SC | 0 - 1 | Portuguese Benfica |
| A45* | Wed, Jul-21 | 6:30 pm | Ernestown SS | Pilot House LCFC I | 1 - 2 | Portuguese Benfica |
| A47 (f) | Wed, Jul-28 | 6:30 pm | Caton's 2 | Soccer Plus FC | 3 - 0 | Portuguese Benfica |
| A51 | Wed, Aug-04 | 6:30 pm | Ernestown SS | LCFC II | 0 - 8 | Portuguese Benfica |
| A56 | Wed, Aug-11 | 6:00 pm | Caton's 2 | Portuguese Benfica | 3 - 2 | Cataraqui I |
| A61 | Wed, Aug-18 | 8:30 pm | Woodbine 5 | Portuguese Benfica | 3 - 3 | AS Roma |
| A68 | Wed, Aug-25 | 8:30 pm | Woodbine 5 | Portuguese Benfica | 5 - 3 | The Keg FC |
| AP2 (f) | Sun, Aug-29 | 6:30 pm | Woodbine 4 | Portuguese Benfica | 3 - 0 | LCFC II |
| AP5 | Tue, Aug-31 | 8:30 pm | Woodbine 5 | AS Roma | 1 - 1 | Portuguese Benfica |
| Penalty Kicks | (0 - 3) | |||||
| AP6 | Thu, Sep-02 | 6:30 pm | Woodbine 5 | Pilot House LCFC I | 0 - 2 | Portuguese Benfica |