Born into a footballing family, Sammy Winston started his career at Spurs, but moved around in non-league circles for much of his career.
Despite being born of an Arsenal professional father, Sammy was brought through the Spurs Youth system, he was part of the Southern Junior Floodlit Cup winning side of 1993, but failed to make the professional grade and moved onto Norwich City's youth set-up in 1995.
The move didn't work out for him, so he returned to London with Leyton Orient and did well for their youth and reserve sides, eventually playing in the Football League for The O's on 11 occasions before moving into non-league with Yeovil Town in the summer of 1997. Winston scored well there, but was allowed to go back nearer home, when he signed for Chesham United. He was farmed out on loan to Sutton United in the summer of 1999, with a permanent deal following shortly after.
His time at Sutton saw them relegated from the Conference, but he was able to play at that level again when he was transferred to Kingstonian, but they suffered the same fate as Sutton and went down to the Rymans League. As they were unable to keep hold of their well-paid players, Winston was let go in October 2001, but he managed to get a deal at Slough Town in November 2001. He was at the club for a season and a half before returning once more to North London with Boreham Wood.
Here Sammy had a profitable time in their forward line, almost breaking the club's goal-scoring record for goals in a season, but changes in management and striking partners saw him transfer listed and then move to East Thurrock United in February 2005.
At the start of the new season, Sammy had moved on again, this time to Harlow Town. Seven months later, the striker had turned up at Uxbridge on loan and finally left Harlow at the end of the 2006-07 season to join Rymans League rivals Leyton. However, the money behind the East London club dried up and many players left, including Winston, who returned to Harlow Town.
From there, Sammy moved to Potters Bar Town and then linked up with Steve Brown (having worked with him before at Slough Town, Boreham Wood and Potters Bar Town) at Enfield Town, where he was assistant manager, in February 2009.
Away from the game, Winston worked with the Fire Brigade.