| Saturday 9th May 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Ryde CC 2nd XI Saturday |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Sunday 10th May 2026 at 10:00 | Steephill | |
| Ventnor CC Under 11 | v | Ryde CC Under 11 |
| Isle of Wight Junior Competitions | Isle of Wight U11 Friendlies | |
| Monday 8th June 2026 at 18:00 | Steephill | |
| Ventnor CC Under 13 | v | Ryde CC Ridgebacks |
| Isle of Wight Junior Competitions | Isle of Wight U13 League | |
| Tuesday 9th June 2026 at 18:00 | Ryde Cricket Club | |
| Ryde CC Ravens | v | Ventnor CC Girls Under 13 |
| Isle of Wight Junior Competitions | Isle of Wight U13 Girls League | |
| Wednesday 17th June 2026 at 18:00 | Steephill | |
| Ventnor CC Girls Under 11 | v | Ryde CC Raccoons |
| Isle of Wight Junior Competitions | Isle of Wight U11 Girls League | |
| Wednesday 17th June 2026 at 18:00 | Ryde Cricket Club | |
| Ryde CC Rattlers | v | Ventnor CC Under 15 |
| Isle of Wight Junior Competitions | Isle of Wight U15 League | |
| Friday 26th June 2026 at 18:00 | Newclose County Cricket Ground | |
| Ventnor CC Girls Under 16 | v | Ryde CC Royals |
| Isle of Wight Junior Competitions | Isle of Wight U16 Girls 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 | |
| Thursday 2nd July 2026 at 18:00 | Steephill | |
| Ventnor CC Women's 1st XI | v | Ryde CC Womens 1st XI |
| Isle of Wight Cricket League | Isle of Wight Women's League | |
| Tuesday 7th July 2026 at 18:00 | Steephill | |
| Ventnor CC Girls Under 13 | v | Ryde CC Ravens |
| Isle of Wight Junior Competitions | Isle of Wight U13 Girls League | |
| Wednesday 15th July 2026 at 18:00 | Steephill | |
| Ventnor CC Under 15 | v | Ryde CC Rattlers |
| Isle of Wight Junior Competitions | Isle of Wight U15 League | |
| Tuesday 4th August 2026 at 18:00 | Ryde Cricket Club | |
| Ryde CC Raccoons | v | Ventnor CC Girls Under 11 |
| Isle of Wight Junior Competitions | Isle of Wight U11 Girls League | |
| Monday 24th August 2026 at 18:00 | Ryde Cricket Club | |
| Ryde CC Royals | v | Ventnor CC Girls Under 16 |
| Isle of Wight Junior Competitions | Isle of Wight U16 Girls League | |
| Tuesday 25th August 2026 at 18:00 | Ryde Cricket Club | |
| Ryde CC Womens 1st XI | v | Ventnor CC Women's 1st XI |
| Isle of Wight Cricket League | Isle of Wight Women's League | |
| Saturday 29th August 2026 at 13:00 | Ryde Cricket Club | |
| Ryde CC 2nd XI Saturday | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 |