Portuguese Benfica's cup games
| Game | Date ↑ | Time | Field | Home | Visitors | |
|---|---|---|---|---|---|---|
| L1 | Fri, Jun-06 | 6:30 pm | Caton's 1 | Cataraqui I | 3 - 1 | The Keg FC |
| L2 | Fri, Jun-06 | 6:30 pm | W J Henderson | Glenhaven United | 1 - 3 | Soccer Plus FC |
| L4 (f) | Fri, Jun-06 | 6:30 pm | Woodbine 4 | Pilot House Nooners | 0 - 3 | AS Roma |
| L6 | Fri, Jun-06 | 6:30 pm | Woodbine 5 | Pilot House LCFC I | 1 - 2 | Portuguese Benfica |
| L3 | Fri, Jun-06 | 8:30 pm | W J Henderson | Overtime FC | 5 - 0 | Cataraqui II |
| L5 | Fri, Jun-06 | 8:30 pm | Woodbine 4 | Portsmouth Celtic FC | 1 - 1 | Grizzly's |
| L7 | Fri, Jun-06 | 8:30 pm | Woodbine 5 | Napanee FC | 2 - 0 | Ryatt United SC |
| L10 | Fri, Jun-20 | 6:30 pm | Woodbine 5 | Pilot House Nooners | 2 - 4 | Portsmouth Celtic FC |
| L8 | Fri, Jun-20 | 6:30 pm | Woodbine 4 | Glenhaven United | 0 - 0 | Overtime FC |
| N6* | Fri, Jun-20 | 6:30 pm | Caton's 1 | AIC | 1 - 6 | Chez Piggy FC |
| N7 | Fri, Jun-20 | 6:30 pm | W J Henderson | Azores Eagles SC | 3 - 0 | CFB Kingston |
| L9 | Fri, Jun-20 | 8:30 pm | Woodbine 4 | Soccer Plus FC | 7 - 1 | Cataraqui II |
| N8 (f) | Fri, Jun-20 | 8:30 pm | W J Henderson | Cataraqui III | 3 - 0 | Frontenac United |
| L12 | Fri, Jun-27 | 6:30 pm | Woodbine 4 | The Keg FC | 1 - 1 | Valhalla |
| L13 | Fri, Jun-27 | 6:30 pm | W J Henderson | Pilot House LCFC I | 5 - 2 | Napanee FC |
| N11 | Fri, Jun-27 | 6:30 pm | Caton's 1 | JKL Rangers | 1 - 4 | Westend Dental |
| N9 | Fri, Jun-27 | 6:30 pm | Woodbine 5 | WTC Pilot House LCFC 2 | 2 - 3 | Loyal Oarsman |
| L14 (f) | Fri, Jun-27 | 8:30 pm | W J Henderson | Portuguese Benfica | 3 - 0 | Ryatt United SC |
| N10 | Fri, Jun-27 | 8:30 pm | Woodbine 5 | SPFC 2 | 1 - 4 | Eastron Tap House |
| N12 | Fri, Jun-27 | 8:30 pm | Caton's 1 | Kingston Athletic | 6 - 0 | Barr Homes FC |
| N1* | Wed, Jul-02 | 6:30 pm | Barr Homes 2 | WTC Pilot House LCFC 2 | 3 - 0 | SPFC 2 |
| N2* | Wed, Jul-02 | 6:30 pm | Barr Homes 3 | Loyal Oarsman | 0 - 1 | Eastron Tap House |
| L15 | Fri, Jul-04 | 6:30 pm | Caton's 1 | Cataraqui II | 3 - 3 | Glenhaven United |
| N13 | Fri, Jul-04 | 6:30 pm | Woodbine 4 | Clippers-Scarpazza Design | 1 - 1 | AIC |
| N15 | Fri, Jul-04 | 6:30 pm | Woodbine 5 | Azores Eagles SC | 5 - 0 | Cataraqui III |
| N4* | Fri, Jul-04 | 6:30 pm | W J Henderson | Westend Dental | 2 - 2 | Barr Homes FC |
| L16 | Fri, Jul-04 | 8:30 pm | Caton's 1 | Overtime FC | 1 - 3 | Soccer Plus FC |
| N14 (f) | Fri, Jul-04 | 8:30 pm | Woodbine 4 | Cancoil Benfica | 3 - 0 | Chez Piggy FC |
| N16 | Fri, Jul-04 | 8:30 pm | Woodbine 5 | CFB Kingston | 3 - 1 | Frontenac United |
| L11* | Sun, Jul-06 | 6:00 pm | Barr Homes 3 | AS Roma | 9 - 1 | Grizzly's |
| N3* | Wed, Jul-09 | 6:30 pm | Barr Homes 3 | JKL Rangers | 1 - 4 | Kingston Athletic |
| N5* | Wed, Jul-09 | 6:30 pm | Markers Acres | Clippers-Scarpazza Design | 2 - 4 | Cancoil Benfica |
| L17 | Fri, Jul-11 | 6:30 pm | Caton's 1 | Valhalla | 1 - 2 | Cataraqui I |
| L18 (f) | Fri, Jul-11 | 6:30 pm | W J Henderson | Grizzly's | 3 - 0 | Pilot House Nooners |
| L20 | Fri, Jul-11 | 6:30 pm | Woodbine 4 | Ryatt United SC | 1 - 9 | Pilot House LCFC I |
| N17 | Fri, Jul-11 | 6:30 pm | Woodbine 5 | Eastron Tap House | 0 - 3 | WTC Pilot House LCFC 2 |
| L19 | Fri, Jul-11 | 8:30 pm | W J Henderson | Portsmouth Celtic FC | 1 - 2 | AS Roma |
| L21 | Fri, Jul-11 | 8:30 pm | Woodbine 4 | Napanee FC | 0 - 8 | Portuguese Benfica |
| N18 | Fri, Jul-11 | 8:30 pm | Woodbine 5 | Loyal Oarsman | 0 - 4 | SPFC 2 |
| N19 | Fri, Jul-18 | 6:30 pm | W J Henderson | Barr Homes FC | 3 - 1 | JKL Rangers |
| N21 | Fri, Jul-18 | 6:30 pm | Woodbine 4 | Chez Piggy FC | 3 - 8 | Clippers-Scarpazza Design |
| N23 (f) | Fri, Jul-18 | 6:30 pm | Caton's 1 | Frontenac United | 0 - 3 | Azores Eagles SC |
| N24* | Fri, Jul-18 | 6:30 pm | Caton's 1 | Cataraqui III | 0 - 4 | CFB Kingston |
| N20 | Fri, Jul-18 | 8:30 pm | W J Henderson | Westend Dental | 4 - 4 | Kingston Athletic |
| N22 | Fri, Jul-18 | 8:30 pm | Woodbine 4 | AIC | 0 - 4 | Cancoil Benfica |
| L22 | Fri, Aug-01 | 6:30 pm | Woodbine 4 | Cataraqui I | 4 - 0 | Overtime FC |
| L24 (f) | Fri, Aug-01 | 6:30 pm | Woodbine 5 | AS Roma | 3 - 0 | Pilot House LCFC I |
| L23 (f) | Fri, Aug-01 | 8:30 pm | Woodbine 4 | Soccer Plus FC | 0 - 1 | Valhalla |
| L25 | Fri, Aug-01 | 8:30 pm | Woodbine 5 | Portuguese Benfica | 2 - 0 | Portsmouth Celtic FC |
| N25 | Fri, Aug-08 | 6:30 pm | Woodbine 4 | WTC Pilot House LCFC 2 | 2 - 3 | Westend Dental |
| N27 | Fri, Aug-08 | 6:30 pm | Woodbine 5 | Cancoil Benfica | 0 - 0 | CFB Kingston |
| Penalty Kicks | (4 - 5) | |||||
| N26 | Fri, Aug-08 | 8:30 pm | Woodbine 4 | Kingston Athletic | 0 - 1 | Eastron Tap House |
| N28 | Fri, Aug-08 | 8:30 pm | Woodbine 5 | Azores Eagles SC | 2 - 2 | Clippers-Scarpazza Design |
| Penalty Kicks | (4 - 5) | |||||
| L26* | Fri, Aug-15 | 6:15 pm | Caton's 1 | Cataraqui I | 3 - 1 | AS Roma |
| L27* | Fri, Aug-15 | 8:15 pm | Caton's 1 | Valhalla | 0 - 3 | Portuguese Benfica |
| N30* | Fri, Aug-15 | 8:15 pm | Woodbine 5 | Eastron Tap House | 3 - 1 | Clippers-Scarpazza Design |
| N29* | Wed, Aug-20 | 6:00 pm | Barr Homes 4 | Westend Dental | 3 - 1 | CFB Kingston |
| L28 | Fri, Aug-22 | 6:30 pm | Woodbine 4 | Cataraqui I | 0 - 2 | Portuguese Benfica |
| N31 | Fri, Aug-22 | 6:30 pm | Woodbine 5 | Westend Dental | 2 - 0 | Eastron Tap House |