His acting credits include the 1968 stage musical Hair and the 1972 Doctor Who serial Day of the Daleks.

In early 1965, Winston, along with his acquaintance Steve Marriott, formed Small Faces with Ronnie Lane and Kenney Jones.

[2] Winston was fundamental in the band's emergence, as his parents owned the Ruskin Arms pub located in Manor Park, a place where the group would rehearse and occasionally perform.

[2] The band released their debut single "Whatcha Gonna Do About It" later that year, peaking at number 14.

Lane stated in an interview that he was fired: Our original organist, Jimmy Winston, wasn't working out.