The son of ex-Arsenal professional Tony Winston, Sam is a midfielder
who began his career as a trainee with Tottenham Hotspur. Whilst
as a 15 year old Associate Schoolboy, he was part of the Spurs
squad that reached the final of the Southern Junior Floodlit Cup.
He transferred his traineeship to Carrow Road in the summer of
1995 as he felt he had a better chance with a smaller club.
Alas this was not to be and Sam returned to London with Leyton
Orient. He did however make 36 appearances for the youth team
in the 1995/96 season scoring 9 goals. Three appearances, all
as substitute, were made for the Reserves. Sam made 11 league
appearances for Orient by the end of the 1996/97 season but joined
Conference side Yeovil. Despite a successful goals per game ratio
for Yeovil, Sam was allowed to return to North London and join
The June 1999 edition of Team Talk magazine revealed that
Sam had joined Sutton United on loan and this later became permanent.
Despite regularly scoring throughout 1999/2000, Sammy's goals
could not prevent Sutton being relegated from the Conference.
However Sammy returned to the Conference in July 2000 when he
signed for Kingstonian. He showed his potential by netting Kingstonian's
only goal in a 3-1 defeat against Chelsea on 22nd July 2000 with
the Blues fielding £15million Jimmy Floyd Hasselbaink, £4million
Einur Gudjohnsen, £5million Mario Stanic, Roberto Di Matteo etc.
Sammy suffered another relegation in April 2001 when Kingstonian
followed Sutton out of the Conference and into the Rymans League.
The resulting financial chaos that Kingstonian suffered saw them
release their highest earners, including Sammy, in October 2001.
Sammy quickly found a new club signing for Slough Town on the
9th November 2001. His stay at Slough lasted approximately 18months
as he switched to Boreham Wood at the end of June 2003.
Sammy scored 58 goals in a staggering 94 starts for the club
between June 2003 and February 2005. In 2003/4 Winston bagged
41 goals just four short of Shaun Marshall's club record haul
in the 1997/98 season. Following the departure of former manager
Steve Browne, Winston stayed loyal to the club, choosing not to
join the exodus of players that Browne commanded. Winston started
the 2004/5 season in a similar vein, hitting 13 goals in as many
starts, with hopes high for another scintillating season, after
forging a fine partnership with Robbie Reinelt. However the club's
decision to release Reinelt and two short-lived partnerships with
Wayne Cort and Miguel De Souza unsettled the striker. Ian Cooper's
arrival sparked a resurrection in Winston's goalscoring appetite,
netting five times in six games. But when Cooper joined Waltham
Forest, Winston was left in a lone striker role, and his lack
of support had an adverse effect on the man who scooped both the
Supporters' and Chairman's Player of the Year Awards last season.
Following a three-match ban he received for a rather harsh sending-off
against Fisher Athletic back in December and a poor run of form,
Sammy was transfer-listed by chairman Danny Hunter in January
2005 , 'to get a reaction'. The striker was the subject of huge
interest from a number of clubs. Sammy opted to join East Thurrock
United towards the end of February 2005. United manager Lee Patterson
works with Sammy on the London Fire Brigade.
The following August saw Sammy playing for Harlow Town. In March
2006, Sammy joined Uxbridge on loan. Although Sammy was Harlow's
leading goalscorer in the 2006/7 season, he was allowed to join
Ryman League side Leyton in the summer of 2007.
After playing for Potters Bar Town during the beginning part
of the 2008/9 season, Sammy joined Enfield Town in early February
2009 whom have the aforementiond Steve Browne as Assistant Manager.