Missing Lee Togwell, Ben Harris, Ryan Bird, Jonathan North and Joe Dandy, the Rebels named an 18-man squad which included two trialists - and one was on target in the second half, sliding in to meet a cross from Johnny Goddard at the near post.
The lead was doubled twelve minutes later with Goddard again the provider - this time crossing in for an unmarked Elliot Benyon to sidefoot home.
Winchester had chances to open the scoring in the first half, with Bentley forcing Rhys Forster into a good save six yards out.
In the second half, the visitors' Herbert took aim from 25 yards and stung the palms of Forster, but the goalkeeper was able to hold onto his clean sheet.
Next up for the Rebels is a home match against National League side Aldershot Town on Saturday morning, with kick-off at the earlier time of 11am.
Image: George Beck
Slough Town Line up
Rhys Forster, Josh Jackman, Gabe George, George Wells, Trialist, Guy Hollis, Edon Pruti, Scott Davies, Matthew Lench, George Hunt, Fabio Sole, Aaron Kuhl, Johnny Goddard, James Dobson, Imran Kayani, Trialist, Elliot Benyon, Manny Williams.