The son of evangelical preacher Octavius Winslow and Hannah Ann Ring, he was born at Leamington, Warwickshire.
Winslow made his first-class debut for Sussex against Gloucestershire in 1875 at the County Ground, Hove.
[2] His second first-class appearance came shortly after this match, for the Marylebone Cricket Club against Cambridge University at Lord's.
In 1891 he was runner-up at the inaugural South African Championships tennis tournament in Port Elizabeth.
Charles' son and Lyndhurst's grandson, Paul, would play Test cricket for South Africa.