SEASON 2018/2019
First Round
| COWES SPORTS | 2-1 | Pan Sports |
| EAST COWES VICS | 1-0 | Northwood St Johns |
| NEWPORT IoW | 1-0 | Shanklin |
| Ventnor | 1-6 | Whitecroft & Barton Sports |
Semi Final
| COWES SPORTS | 1-1 | Whitecroft & Barton Sports |
| Whitecroft & Barton Sports won 3-1 on penalties | ||
| EAST COWES VICTORIA | 1-5 | NEWPORT IoW |
Final
| Whitecroft & Barton Sports | 1-6 | NEWPORT IoW |