| Tuesday 5th May 2026 at 18:00 | Arreton CC | |
| Arreton CC The Hundred | v | Ventnor CC The Hundred |
| Isle of Wight Cricket League | Isle of Wight Midweek 100 League | |
| Monday 29th June 2026 at 18:00 | Ryde Cricket Club | |
| Ryde CC The Hundred | v | Ventnor CC The Hundred |
| Isle of Wight Cricket League | Isle of Wight Midweek 100 League |