Winston was British and had previously coached the Blackheath Harriers rugby team in England.

He was also a "bantam boxer" and trainer for an athletic club in London, before coming to the United States in 1883.

[6] He was the first coach of the Syracuse and Georgia football teams to receive a salary.

[7] During his single season at Georgia in 1894, Winston's team compiled a record of 5–1 including a win against the Auburn Tigers.

This biographical article relating to a college football coach first appointed in the 1890s is a stub.