All Competitions
| Game | Date ↑ | Time | Field | Home | Visitors | |
|---|---|---|---|---|---|---|
| A3 | Wed, May-23 | 6:30 pm | John Machin Turf | Portuguese Benfica | 2 - 0 | Kingston Blues FC |
| A6 | Wed, May-30 | 6:30 pm | Barr Homes 4 | Kingston Hot Fire | 4 - 1 | Portuguese Benfica |
| A14 | Wed, Jun-20 | 6:30 pm | Barr Homes 4 | Portsmouth Celtic FC | 2 - 3 | Portuguese Benfica |
| A18 | Wed, Jun-27 | 6:30 pm | John Machin Turf | Portuguese Benfica | 1 - 4 | Limestone City FC |
| A20 | Wed, Jul-04 | 6:30 pm | Barr Homes 4 | Glenhaven United | 2 - 7 | Portuguese Benfica |
| L1 | Fri, Jul-06 | 6:30 pm | W J Henderson | Portuguese Benfica | 4 - 2 | Glenhaven United |
| A27 | Wed, Jul-18 | 6:30 pm | Barr Homes 4 | Portuguese Benfica | 1 - 1 | Kingston Hot Fire |
| L8* | Tue, Jul-24 | 6:30 pm | Barr Homes 2 | Portuguese Benfica | 2 - 3 | Boca Nooners |
| A31 | Wed, Aug-01 | 6:00 pm | Barr Homes 3 | Boca Nooners | 2 - 1 | Portuguese Benfica |
| A35 | Wed, Aug-08 | 6:00 pm | Barr Homes 2 | Portuguese Benfica | 5 - 2 | Portsmouth Celtic FC |
| A24* | Fri, Aug-17 | 6:30 pm | Woodbine 5 | Kingston Blues FC | 0 - 7 | Portuguese Benfica |
| A39* | Tue, Aug-21 | 6:00 pm | Barr Homes 4 | Limestone City FC | 8 - 0 | Portuguese Benfica |
| A41 | Wed, Aug-22 | 6:00 pm | Barr Homes 3 | Portuguese Benfica | 2 - 1 | Glenhaven United |
| A10* | Fri, Aug-24 | 6:30 pm | Woodbine 5 | Portuguese Benfica | 1 - 0 | Boca Nooners |
| A44 | Wed, Aug-29 | 6:00 pm | Barr Homes 3 | Portuguese Benfica | 2 - 2 | Glenhaven United |
| Penalty Kicks | (4 - 5) |