[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.
[12] 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.
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.
[20][21] Prior to the 2013–14 season, Central FC and Walsall of Football League One agreed to a partnership that featured the Saddlers' in a pre-season tour of Trinidad and Tobago.
[22] As part of their agreement, Winchester was one of five one-week trialists at Walsall during its training sessions and exhibition matches against his previous club Stokely Vale and a Pro League XI.
He wanted the ball, he took people on, he got the penalty and for me that is the making of a player for the future.Winchester made his full international debut for the Trinidad and Tobago national team,[2] on 15 October 2013, at the age of 19, in a match against New Zealand after coming on as a second-half substitute for captain Kenwyne Jones.
[39] In the return match in Port of Spain, Winchester came on as a substitute for Lester Peltier and helped draw a penalty kick that led to the team's second goal.
[40][41] On 4 June 2014, Winchester made a late substitute appearance in a 3–0 loss during a send-off series match for Argentina at Estadio Monumental prior to the 2014 FIFA World Cup.