| Saturday 25th April 2026 at 13:00 | IOW Community Club | |
| Cowes CC 1st XI | v | Ventnor CC Friendly XI |
| Saturday 30th May 2026 at 13:00 | IOW Community Club | |
| Cowes CC 1st XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Saturday 4th July 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Cowes CC 1st XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 |