Cup Competitions
| The Harwoods DACIA Senior (Gold) Cup | ||||
| 1st Round | ||||
| Ventnor | 2 | - | 2 | Northwood |
| 2nd Round | ||||
| Brading Town | 7 | - | 1 | Bembridge |
| High park | A | / | W | Binstead & COB |
| Ventnor / W & B | v | West Wight | ||
| 3rd Round | ||||
| Cowes Sport | v | W & B | ||
| East Cowes Vics | 3 | - | 3 | Brading Town |
| Brading won on Penalties | ||||
| Newport | 4 | - | 1 | Vectis |
| Binstead & COB | v | Shanklin | ||
| Semi-Final | ||||
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|
Challenge Cup Sponsored by Island Echo |
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| 1st Round | ||||
| East Cowes Vics Dev | 3 | - | 4 | Brading Town |
| Ventnor | 3 | - | 2 | Cowes Res |
| Vectis | 3 | - | 0 | Northwood SJ |
| West Wight | 1 | - | 2 | W & B |
| Shanklin | 1 | - | 1 | High Park |
| Shanklin won on penalties | ||||
| 2nd Round | ||||
| Vectis | 2 | - | 2 | Binstead |
| Binstead won on penalties | ||||
| Ventnor | 4 | - | 2 | Brading Town |
| Shanklin | 1 | - | 2 | W & B |
| ECS | 3 | - | 7 | Bembridge |
| Semi Final | ||||
| Binstead & COB | 3 | - | 3 | Ventnor |
| Ventnor won on penalties | ||||
| W & B | 1 | - | 0 | Bembridge |
| Final | ||||
| W & B | 3 | - | 3 | Ventnor |
| W & B won on penalties | ||||
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|
Memorial Cup |
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| 1st Round | ||||
| Newchuch | 0 | - | 2 | Sandown & Lake |
| Seaview | 0 | - | 12 | Osborne Coburg |
| 2nd Round | ||||
| Ryde Saints | 0 | - | 2 | Sandown & Lake |
| Newport Reserves | 1 | - | 3 | Osborne Coburg |
| Bye : AFC Wooton / Niton Community | ||||
| 3rd Round | ||||
| Ventnor | 2 | - | 2 | Bembridge |
| Ventnor win on penalties | ||||
| AFC Wootton | 1 | - | 7 | Brading Town |
| Binstead | 3 | - | 4 | Shanklin |
| Northwood | 5 | - | 0 | Sandown |
| W & B | 3 | - | 0 | Osborne Coburg |
| West Wight | 3 | - | 3 | Vectis |
| Vectis won on penalties | ||||
| E.C.S | v | High Park | ||
| Quarter Final | ||||
| Brading Town | 0 | - | 2 | Ventnor |
| Shanklin | v | W & B | ||
| High Park | v | Northwood | ||
| Vectis | 3 | - | 2 | Cowes Res |
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|
Ken Morris Junior A Cup sponsored by the Harwoods Saturday League |
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| 1st Round | ||||
| Osborne Coburg | 8 | - | 3 | Niton Community |
| Ventnor Res | 0 | - | 3 |
Sandown & Lake |
| Newport Res | 5 | - | 2 | Sandown & Lake Res |
| Newchurch | 1 | - | 2 | Brading Town Res |
| Seaview | 0 | - | 5 | AFC Wootton |
| Binstead & COB Res | 6 | - | 0 | Shanklin Res |
| Carisbrooke Utd | A | / | W | Osborne Coburg Res |
| Ryde Saints | 1 | - | 5 | Bembridge Res |
| Northwood St. John Res | 1 | - | 2 | W & B Res |
| West Wight Res | v | Vectis Res | ||
| 2nd Round | ||||
| Osborne Coburg | 2 | - | 0 | W & B Res |
| Bembridge Res | 3 | - | 1 | Vectis Res |
| Newport Res | 3 | - | 2 |
Sandown & Lake |
| All Other matches - BYE | ||||
| 3rd Round | ||||
| Osborne Coburg | 9 | - | 4 | Newport Res |
| Osborne Coburg Res | H | / | W | Brading Res |
| AFC Wootton | 7 | - | 1 | Binstead Res |
| ECS Res | 2 | - | 0 | Bembridge Res |
| 4th Round | ||||
| Osborne Coburg | 11 | - | 0 | Osborne Coburg Res |
| ECS Res | 1 | - | 2 | AFC Wooton |
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| The UNISON Junior B Cup | ||||
| 1st Round | ||||
| Ventnor “A” | A | - | W | AFC Wootton Res |
| 2nd Round | ||||
|
Ventnor A / AFC Wootton Res |
v | Bembridge A | ||
| Ryde Saints Res | 0 | - | 2 | High Park Res |
|
Newchurch Res |
0 | - | 6 |
West Wight A |
|
Seaview Res |
0 | - | 5 |
Niton Community Res |
| Semi - Final | ||||
| West Wight A | v | AFC Wootton Res / Bembridge A | ||
| Niton | 1 | - | 1 | High Park Res |
| High Park Res won on Penalties | ||||
| Final | ||||
| High Park Res | v | |||
