| Saturday 2nd May 2026 at 13:00 | Northwood Cricket Club | |
| Northwood CC, IOW 2nd XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Saturday 23rd May 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Northwood CC, IOW 2nd XI |
| Isle of Wight Cricket League | Fred Winter Cup | |
| Saturday 18th July 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Northwood CC, IOW 2nd XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 |