| Saturday 25th April 2026 at 13:00 | Shanklin & Godshill Cricket Club | |
| Shanklin & Godshill CC 1st XI | v | Ventnor CC 2nd XI |
| Saturday 2nd May 2026 at 13:00 | The David Roth Cricket Ground | |
| Easton & Martyr Worthy CC 1st XI | v | Ventnor CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 9th May 2026 at 13:00 | Recreation Ground | |
| Rowledge CC 2nd XI | v | Ventnor CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 16th May 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | Burridge CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Sunday 17th May 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | Singh XI CC, Southampton Friendly XI |
| Saturday 23rd May 2026 at 13:00 | St James | |
| Portsmouth and Southsea CC 2nd XI | v | Ventnor CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 30th May 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | Steep CC 1st XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 6th June 2026 at 13:00 | The Alan Taylor Field | |
| St Cross Symondians CC 3rd XI | v | Ventnor CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 13th June 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | Hayling Island CC 1st XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 20th June 2026 at 13:00 | Shanklin & Godshill Cricket Club | |
| Shanklin & Godshill CC 1st XI | v | Ventnor CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 27th June 2026 at 13:00 | Hunter Park | |
| Twyford CC, Hants 1st XI | v | Ventnor CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 4th July 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | Easton & Martyr Worthy CC 1st XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 11th July 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | Rowledge CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 18th July 2026 at 13:00 | Burridge Cricket Club | |
| Burridge CC 2nd XI | v | Ventnor CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 25th July 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | Portsmouth and Southsea CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 1st August 2026 at 13:00 | Steep Cricket Club | |
| Steep CC 1st XI | v | Ventnor CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 8th August 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | St Cross Symondians CC 3rd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 15th August 2026 at 13:00 | Hayling Park | |
| Hayling Island CC 1st XI | v | Ventnor CC 2nd XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 22nd August 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | Shanklin & Godshill CC 1st XI |
| Hampshire Cricket League | Division 2B | |
| Saturday 29th August 2026 at 13:00 | Steephill | |
| Ventnor CC 2nd XI | v | Twyford CC, Hants 1st XI |
| Hampshire Cricket League | Division 2B |