| Friday 24th April 2026 at 17:00 | Steephill | |
| Ventnor CC 3rd XI | v | West Ilsley CC 1st XI |
| Saturday 2nd May 2026 at 13:00 | Shanklin & Godshill Cricket Club | |
| Shanklin & Godshill CC 2nd XI | v | Ventnor CC 3rd XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 | |
| Saturday 9th May 2026 at 13:00 | Smallbrook Stadium | |
| Wight Whizzers CC 1st XI | v | Ventnor CC 3rd XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 | |
| Saturday 16th May 2026 at 13:00 | Northwood Cricket Club | |
| Northwood CC, IOW 1st XI | v | Ventnor CC 3rd XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 | |
| Saturday 23rd May 2026 at 13:00 | Porchfield Cricket Club | |
| Ventnor CC 3rd XI | v | Wight Whizzers CC 1st XI |
| Isle of Wight Cricket League | Senior Cup Group Stage | |
| Saturday 30th May 2026 at 13:00 | Shanklin & Godshill Cricket Club | |
| Shanklin & Godshill CC 2nd XI | v | Ventnor CC 3rd XI |
| Isle of Wight Cricket League | Senior Cup Group Stage | |
| Saturday 6th June 2026 at 13:00 | The Green | |
| St Helens CC, Isle of Wight 1st XI | v | Ventnor CC 3rd XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 | |
| Saturday 13th June 2026 at 13:30 | Brading CC | |
| Ventnor CC 3rd XI | v | Newport CC, Isle of Wight 1st XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 | |
| Saturday 27th June 2026 at 13:30 | Brading CC | |
| Ventnor CC 3rd XI | v | Northwood CC, IOW 1st XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 | |
| Saturday 4th July 2026 at 13:00 | The Green | |
| St Helens CC, Isle of Wight 1st XI | v | Ventnor CC 3rd XI |
| Isle of Wight Cricket League | Senior Cup Group Stage | |
| Saturday 11th July 2026 at 13:00 | Northwood Cricket Club | |
| Northwood CC, IOW 1st XI | v | Ventnor CC 3rd XI |
| Isle of Wight Cricket League | Senior Cup Group Stage | |
| Saturday 18th July 2026 at 13:00 | TBC | |
| Ventnor CC 3rd XI | v | Shanklin & Godshill CC 2nd XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 | |
| Saturday 25th July 2026 at 13:00 | Porchfield Cricket Club | |
| Ventnor CC 3rd XI | v | Wight Whizzers CC 1st XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 | |
| Saturday 1st August 2026 at 13:00 | Newclose County Cricket Ground | |
| Newport CC, Isle of Wight 1st XI | v | Ventnor CC 3rd XI |
| Isle of Wight Cricket League | Senior Cup Group Stage | |
| Saturday 8th August 2026 at 13:00 | Porchfield Cricket Club | |
| Ventnor CC 3rd XI | v | St Helens CC, Isle of Wight 1st XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 | |
| Saturday 15th August 2026 at 13:00 | Newclose County Cricket Ground | |
| Newport CC, Isle of Wight 1st XI | v | Ventnor CC 3rd XI |
| Isle of Wight Cricket League | Isle of Wight Division 1 |