| 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 | |
| Wednesday 13th May 2026 at 18:00 | Arreton CC | |
| Arreton CC Rebels | v | Ventnor CC Girls Under 13 |
| Isle of Wight Junior Competitions | Isle of Wight U13 Girls League | |
| Thursday 14th May 2026 at 18:00 | Arreton CC | |
| Arreton CC Womens 1st XI | v | Ventnor CC Women's 1st XI |
| Isle of Wight Cricket League | Isle of Wight Women's League | |
| Wednesday 27th May 2026 at 18:00 | Arreton CC | |
| Arreton CC U16 Rebels | v | Ventnor CC Girls Under 16 |
| Isle of Wight Junior Competitions | Isle of Wight U16 Girls League | |
| Sunday 7th June 2026 at 10:00 | Steephill | |
| Ventnor CC Under 11 | v | Arreton CC Hawks |
| Isle of Wight Junior Competitions | Isle of Wight U11 Cup | |
| Wednesday 10th June 2026 at 18:00 | Steephill | |
| Ventnor CC Under 15 | v | Arreton CC Buzzards |
| Isle of Wight Junior Competitions | Isle of Wight U15 League | |
| Thursday 11th June 2026 at 18:00 | Steephill | |
| Ventnor CC Midweek XI | v | Arreton CC Friendly XI |
| Sunday 14th June 2026 at 10:00 | Steephill | |
| Ventnor CC Under 11 | v | Arreton CC Falcons |
| Isle of Wight Junior Competitions | Isle of Wight U11 Friendlies | |
| Saturday 27th June 2026 at 13:00 | Arreton CC | |
| Arreton CC 1st XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Wednesday 15th July 2026 at 18:00 | Arreton CC | |
| Arreton CC Rebels Young Guns | v | Ventnor CC Girls Under 11 |
| Isle of Wight Junior Competitions | Isle of Wight U11 Girls League | |
| Sunday 26th July 2026 at 11:00 | Arreton CC | |
| Arreton CC Hawks | v | Ventnor CC Under 11 |
| Isle of Wight Junior Competitions | Isle of Wight U11 Friendlies | |
| Thursday 6th August 2026 at 18:00 | Steephill | |
| Ventnor CC Girls Under 16 | v | Arreton CC U16 Rebels |
| Isle of Wight Junior Competitions | Isle of Wight U16 Girls League | |
| Monday 10th August 2026 at 18:00 | Arreton CC | |
| Arreton CC Eagles | v | Ventnor CC Under 13 |
| Isle of Wight Junior Competitions | Isle of Wight U13 League | |
| Tuesday 11th August 2026 at 18:00 | Steephill | |
| Ventnor CC Girls Under 13 | v | Arreton CC Rebels |
| Isle of Wight Junior Competitions | Isle of Wight U13 Girls League | |
| Wednesday 12th August 2026 at 18:00 | Steephill | |
| Ventnor CC Girls Under 11 | v | Arreton CC Rebels Young Guns |
| Isle of Wight Junior Competitions | Isle of Wight U11 Girls League | |
| Wednesday 12th August 2026 at 18:00 | Arreton CC | |
| Arreton CC Buzzards | v | Ventnor CC Under 15 |
| Isle of Wight Junior Competitions | Isle of Wight U15 League | |
| Saturday 15th August 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Arreton CC 1st XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Monday 17th August 2026 at 18:00 | Steephill | |
| Ventnor CC Women's 1st XI | v | Arreton CC Womens 1st XI |
| Isle of Wight Cricket League | Isle of Wight Women's League |