| Saturday 24th May 2025 at 13:30 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Northwood CC, IOW 2nd XI |
| Isle of Wight Cricket League | Fred Winter Cup Group A | |
| Saturday 31st May 2025 at 13:30 | Brading CC | |
| Shanklin & Godshill CC 3rd XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Eastmount Hall Hotel Isle of Wight Division 2 | |
| Saturday 7th June 2025 at 13:30 | IOW Community Club | |
| Cowes CC 1st XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Fred Winter Cup Group A | |
| Saturday 14th June 2025 at 13:30 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Shanklin & Godshill CC 2nd XI |
| Isle of Wight Cricket League | Eastmount Hall Hotel Isle of Wight Division 2 | |
| Saturday 28th June 2025 at 13:30 | Arreton CC | |
| Arreton CC 1st XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Eastmount Hall Hotel Isle of Wight Division 2 | |
| Saturday 5th July 2025 at 13:30 | Shanklin & Godshill Cricket Club | |
| Shanklin & Godshill CC 2nd XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Eastmount Hall Hotel Isle of Wight Division 2 | |
| Saturday 12th July 2025 at 13:30 | Northwood Cricket Club | |
| Northwood CC, IOW 2nd XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Fred Winter Cup Group A | |
| Saturday 19th July 2025 at 13:30 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Cowes CC 1st XI |
| Isle of Wight Cricket League | Fred Winter Cup Group A | |
| Saturday 26th July 2025 at 13:30 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Freshwater CC 1st XI |
| Isle of Wight Cricket League | Eastmount Hall Hotel Isle of Wight Division 2 | |
| Saturday 2nd August 2025 at 13:30 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Shanklin & Godshill CC 3rd XI |
| Isle of Wight Cricket League | Eastmount Hall Hotel Isle of Wight Division 2 | |
| Saturday 9th August 2025 at 13:30 | Newclose County Cricket Ground | |
| Newport CC, Isle of Wight 2nd XI | v | Ventnor CC 4th XI |
| Isle of Wight Cricket League | Eastmount Hall Hotel Isle of Wight Division 2 | |
| Saturday 23rd August 2025 at 13:30 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Newport CC, Isle of Wight 2nd XI |
| Isle of Wight Cricket League | Eastmount Hall Hotel Isle of Wight Division 2 | |
| Saturday 30th August 2025 at 13:30 | Arreton C.C. | |
| Ventnor CC 4th XI | v | Northwood CC, IOW 2nd XI |
| Isle of Wight Cricket League | Eastmount Hall Hotel Isle of Wight Division 2 |