| Saturday 2nd May 2026 at 13:00 | Northwood Cricket Club | |
| Northwood CC, IOW 2nd XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| 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 | |
| Saturday 16th May 2026 at 13:00 | Newclose County Cricket Ground | |
| Newport CC, Isle of Wight 2nd XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Saturday 23rd May 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Northwood CC, IOW 2nd XI |
| Isle of Wight Cricket League | Fred Winter Cup | |
| Saturday 30th May 2026 at 13:00 | IOW Community Club | |
| Cowes CC 1st XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Saturday 6th June 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Freshwater CC 1st XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Saturday 13th June 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Shanklin & Godshill CC 3rd XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| 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 | |
| Saturday 4th July 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Cowes CC 1st XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Saturday 18th July 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Northwood CC, IOW 2nd XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Saturday 25th July 2026 at 13:00 | School Field | |
| Freshwater CC 1st XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Saturday 1st August 2026 at 13:00 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Newport CC, Isle of Wight 2nd XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| Saturday 8th August 2026 at 13:30 | Brading CC | |
| Shanklin & Godshill CC 3rd XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Isle of Wight Division 2 | |
| 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 | |
| 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 |