Invited to bat in the first all-day fixture, Ventnor were given a decent start by openers Rob Snell (17) and Ben Woodhouse (30) and at 125-3 looked set to post a 200 plus total.
However, the pre-lunch dismissals of Alex Glendenning (44), Toby Corbin and Neil Westhorpe gave the visitors the upper hand, South African Geoff Dods taking 5-57 as the hosts were dismissed for 166, Alex Horton (14) and Adam Wilson (17) chipping in down the order.
Mark Holmes’ side took a couple of early wickets but 67 from Joe Collings-Wells and 30 from Dods saw the League leaders home with support from Hampshire’s Ryan Stevenson who made 15.
The side travel to Alton on Saturday.
Meanwhile the second team lost heavily by 203 runs at Ropley in Hampshire League Division 1.
Chasing a massive 355-9, Neimand making 139, the youthful Ventnor side could only manage 152 in reply, Ben Clarke (38) and Martin Blackman top scoring.
United Services are the visitors to Steephill on Saturday.
The third team scored an excellent 166 run victory over Challengers of Gosport in Regional Division 3 South.
A terrific unbeaten innings of 152 from young Marcus Horton was the bedrock of Ventnor’s total of 291-2 with Jason Boulter contributing 67 not out.
The visitors were never in the hunt with teenagers Finlay Robertson (3-24), Zeph Wells (2-15) and Horton (2-20) helping to dismiss them for 125.
The side travel to Denmead on Saturday.