| Saturday 25th April 2026 at 13:00 | IOW Community Club | |
| Cowes CC 1st XI | v | Ventnor CC Friendly XI |
| Wednesday 13th May 2026 at 18:00 | IOW Community Club | |
| Cowes CC Under 15 | v | Ventnor CC Under 15 |
| Isle of Wight Junior Competitions | Isle of Wight U15 League | |
| 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 | |
| Monday 15th June 2026 at 18:00 | Steephill | |
| Ventnor CC Under 13 | v | Cowes CC Under 13 |
| Isle of Wight Junior Competitions | Isle of Wight U13 League | |
| 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 | |
| Wednesday 5th August 2026 at 18:00 | Steephill | |
| Ventnor CC Under 15 | v | Cowes CC Under 15 |
| Isle of Wight Junior Competitions | Isle of Wight U15 League | |
| Sunday 16th August 2026 at 10:00 | Steephill | |
| Ventnor CC Under 11 | v | Cowes CC Under 11 |
| Isle of Wight Junior Competitions | Isle of Wight U11 Friendlies |