| Sunday 23rd August 2026 at 10:00 | School Field | |
| Freshwater CC Under 11 | v | Ventnor CC Under 11 |
| Isle of Wight Junior Competitions | Isle of Wight U11 Friendlies | |
| Sunday 23rd August 2026 at 10:30 | Steephill | |
| Ventnor CC Friendly XI | v | Ventnor CC 6 a side |
| 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 | |
| Wednesday 26th August 2026 at 18:00 | Newclose County Cricket Ground | |
| Newport CC, Isle of Wight Girls Under 11 | v | Ventnor CC Girls Under 11 |
| Isle of Wight Junior Competitions | Isle of Wight U11 Girls League | |
| Thursday 27th August 2026 at 17:30 | Steephill | |
| Ventnor CC Evening XI | v | Island Bakeries CC Evening XI |
| Friday 28th August 2026 at 18:00 | Steephill | |
| Ventnor CC Girls Under 13 | v | Newport CC, Isle of Wight Girls Under 13 |
| Isle of Wight Junior Competitions | Isle of Wight U13 Girls League | |
| Saturday 29th August 2026 at 12:00 | Ridge Meadow | |
| Hambledon CC, Hants 1st XI | v | Ventnor CC 1st XI |
| Southern Premier Cricket League | Division 1 | |
| Saturday 29th August 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | Twyford CC, Hants 1st XI |
| Hampshire Cricket League | Division 2B | |
| 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 | |
| Sunday 30th August 2026 at | Steephill | |
| Ventnor CC Sunday 1st XI | v | Reading Lions CC Friendly XI |
| Monday 31st August 2026 at 11:30 | Steephill | |
| Ventnor CC Midweek XI | v | Reading Lions CC 1st XI |
| Tuesday 1st September 2026 at 17:30 | Northwood Cricket Club | |
| Ventnor CC Under 13 | v | Ryde CC Ridgebacks |
| Isle of Wight Junior Competitions | Isle of Wight U13 Plate | |
| Wednesday 2nd September 2026 at 17:00 | Steephill | |
| Ventnor CC The Hundred | v | Shanklin & Godshill CC The Hundred |
| Isle of Wight Cricket League | Isle of Wight 100 League Final | |
| Saturday 5th September 2026 at 13:00 | Stansted Park CC | |
| Stansted Park CC Sunday 1st XI | v | Ventnor CC Friendly XI |
| Saturday 5th September 2026 at 13:00 | Steephill | |
| Ventnor CC Friendly XI | v | Hythe & Dibden CC Sunday 1st XI |
| Sunday 6th September 2026 at 12:30 | Shanklin & Godshill Cricket Club | |
| Ventnor CC 4th XI | v | Newport CC, Isle of Wight 2nd XI |
| Isle of Wight Cricket League | Fred Winter Cup | |
| Sunday 6th September 2026 at 13:00 | Steephill | |
| Ventnor CC Friendly XI | v | Chichester Raquets CC Midweek XI |
| Sunday 6th September 2026 at 13:00 | Goodwood Cricket Club | |
| Goodwood CC Sunday XI | v | Ventnor CC Sunday 1st XI |
| Friday 11th September 2026 at 16:00 | ||
| Ventnor CC Midweek XI | v | Haywards Heath CC Touring XI |
| Saturday 12th September 2026 at 13:00 | Steephill | |
| Ventnor CC Friendly XI | v | Dumbleton CC 1st XI |
| Sunday 13th September 2026 at 13:00 | Steephill | |
| Ventnor CC Friendly XI | v | Egham Roses CC 1st XI |
| Saturday 19th September 2026 at 13:00 | Steephill | |
| Ventnor CC Friendly XI | v | London Knights CC 1st XI |
| Sunday 20th September 2026 at 13:00 | Steephill | |
| Ventnor CC Friendly XI | v | Lampton CC Sunday 1st XI |
| Saturday 26th September 2026 at 12:00 | Steephill | |
| Ventnor CC Friendly XI | v | Ferring CC 1st XI |
| Sunday 27th September 2026 at 12:00 | Steephill | |
| Ventnor CC Friendly XI | v | Luton Caribbean CC Friendly XI |
| Sunday 4th October 2026 at 12:00 | Steephill | |
| Ventnor CC Sunday 1st XI | v | London Theatres CC Sunday 1st XI |