| Saturday 9th May 2026 at 13:00 | Smallbrook Stadium | |
| Wight Whizzers CC 1st XI | v | Ventnor CC 3rd XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 | |
| Saturday 23rd May 2026 at 13:00 | Porchfield Cricket Club | |
| Ventnor CC 3rd XI | v | Wight Whizzers CC 1st XI |
| Isle of Wight Cricket League | Senior Cup Group Stage | |
| Thursday 4th June 2026 at 18:00 | Steephill | |
| Ventnor CC Midweek XI | v | Wight Whizzers CC 1st XI |
| Sunday 21st June 2026 at 14:00 | Steephill | |
| Ventnor CC Friendly XI | v | Wight Whizzers CC 1st XI |
| Saturday 25th July 2026 at 13:00 | Porchfield Cricket Club | |
| Ventnor CC 3rd XI | v | Wight Whizzers CC 1st XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 |