Winchester began his football career in 2011, at the age of 17, for semi-professional club Stokely Vale on the sister-isle of Tobago. In his first season, Winchester was positioned as a winger and scored one league goal.[3] However, his best performances occurred during the TOYOTA Classic in November 2011 where he scored two goals in as many matches to lead his club to the quarterfinals.[4][5] Winchester started the following season for Stokely Vale as a striker and immediately scored two goals in his first three matches.[6][7] However, Rundell did not score again until 5 August 2012 when he recorded the lone goal in a win over Joe Public.[8] In October, Winchester rediscovered his goal-scoring form after recording goals in three consecutive league matches, respectively, against Siparia Spurs,[9] 1.FC Santa Rosa,[10] and Club Sando.[11] He scored a further brace in his next match to bring his league total to eight goals.[12]
edgespro 2012
In November 2012, Winchester gained notoriety around the TT Pro League after scoring three goals to eliminate both Police and Caledonia AIA in consecutive rounds during the TOYOTA Classic.[13][14] In December, he continued his giant-killing in the FA Trophy after leading Stokely Vale to the quarterfinals with victories over Pro League clubs St. Ann's Rangers and Defence Force; having scored a goal in each match.[15][16] In his two seasons with Stokely Vale, Winchester recorded nine league goals and 16 goals in all competitions.
On 20 December 2012, one day after leading Stokely Vale to a win over TT Pro League leaders Defence Force, Winchester completed a move to Central FC on a free transfer.[1] The following night, he scored a 57th-minute goal in his professional debut for the Sharks in a loss to Caledonia AIA.[17] However, after the arrival of Antiguan Peter Byers the next month,[18] playing time was sparse for the remainder of the season. However, in a rare start on 6 May 2013, he provided a brace in a win over Caledonia AIA.[19] Winchester finished his first season with Central FC with a goal in the semifinals of the Digicel Pro Bowl against North East Stars.[20][21] 2ff7e9595c
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