| Thursday 23rd July 2026 at 18:00 | Steephill | |
| Ventnor CC Midweek XI | v | Kettering Southgate CC Friendly XI |
| Tuesday 28th July 2026 at 18:00 | Steephill | |
| Ventnor CC Midweek XI | v | Bedworth CC IOW 2026 Touring XI |
| Wednesday 29th July 2026 at 14:30 | Steephill | |
| Ventnor CC Midweek XI | v | Luddesdowne CC Midweek XI |
| Thursday 30th July 2026 at | Porchfield Cricket Club | |
| Porchfield CC T20 XI | v | Ventnor CC Midweek XI |
| Friday 31st July 2026 at 18:00 | Steephill | |
| Ventnor CC Midweek XI | v | Ventnor Rugby Club |
| Tuesday 11th August 2026 at 18:00 | Northwood Cricket Club | |
| Northwood CC, IOW Evening XI | v | Ventnor CC Midweek XI |
| Tuesday 18th August 2026 at 14:00 | Steephill | |
| Ventnor CC Midweek XI | v | Hurstpierpoint CC 1st XI |
| Thursday 20th August 2026 at 17:00 | Steephill | |
| Ventnor CC Midweek XI | v | White Horse CC 1st XI |
| Monday 31st August 2026 at 11:30 | Steephill | |
| Ventnor CC Midweek XI | v | Reading Lions CC 1st XI |
| Friday 11th September 2026 at 16:00 | ||
| Ventnor CC Midweek XI | v | Haywards Heath CC Touring XI |