| Saturday 6th June 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Freshwater CC 1st XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Monday 6th July 2026 at 18:00 | Steephill | |
| Ventnor CC Under 13 | v | Freshwater CC Under 13 |
| Isle of Wight Junior Competitions | Isle of Wight U13 League | |
| Saturday 25th July 2026 at 13:00 | School Field | |
| Freshwater CC 1st XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Sunday 23rd August 2026 at 10:00 | School Field | |
| Freshwater CC Under 11 | v | Ventnor CC Under 11 |
| Isle of Wight Junior Competitions | Isle of Wight U11 Friendlies |