Winchester, 21, a member of the Trinidad and Tobago National Team, joins Portland from Central FC of the TT Pro League (formerly known as the Professional Football League), the top-flight division of soccer in Trinidad and Tobago. Winchester notched 19 goals in 34 matches (26 starts) in all competitions for Central FC, leading his team to a Lucozade Sport Goal Shield in 2014 and taking both the tournament MVP and Golden Boot honors. Winchester also led his team to a second-place finish in the TT Pro League and was awarded Young Footballer of the Year, Goal of the Season and Supporters Goal of the Season by his own club in 2014. Winchester first appeared for the Trinidad and Tobago National Team as a 19-year-old and has four total caps after making his senior team debut on Oct. 16, 2013, as a substitute against New Zealand.
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