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 | v | Whitecroft & Barton Sports |
| EAST COWES VICTORIA | 1-5 | NEWPORT IoW |
Final
| COWES SPORTS/W&B Sports | v | NEWPORT IoW |