| Thursday 4th June 2026 at 18:00 | Steephill | |
| Ventnor CC The Hundred | v | Wight Whizzers CC The Hundred |
| Isle of Wight Cricket League | Isle of Wight Midweek 100 League | |
| Friday 12th June 2026 at 18:00 | Steephill | |
| Ventnor CC The Hundred | v | Shanklin & Godshill 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 |