five best league players in each of his final two years at Naps, which included a league-leading 16 goals in 2008. Winchester subsequently received the individual award for Best Forward of the Year. Club career W Connection Development and breakthrough (2009–2012) After spending several seasons in the club's youth program, Winchester made his professional football debut in 2009, at the age of 17, for W Connection of the TT Pro League. Shahdon went on to score four goals in seven league appearances for the Savonetta Boys. However, the highlight of his first professional season occurred when he appeared for W Connection during the group stage of the 2009–10 CONCACAF Champions League against Real España. The following season, his goal-scoring form continued with a further five goals in ten appearances, prompting his debut for the Soca Warriors and trials from several clubs abroad. In particular, during a trial in Scotland with Celtic, 18-year-old Winchester scored two goals in a developmental match against a Motherwell XI on 14 September 2010. However, terms ultimately could not be agreed upon. He had further trials at Braga and FC Sevastopol in 2009 and 2010, respectively, followed by trials at FC Dallas and Colorado Rapids of Major League Soccer in 2011. In January 2012, Winchester went on a two-month loan to Sông Lam Nghệ An of V.League 1. However, his international clearance arrived after the transfer window had closed and was unable to make an appearance for the Vietnamese club. Afterwards, Shahdon returned to Trinidad and Tobago to lead W Connection to the club's fourth Pro League championship finishing the 2011–12 season with three goals. In March 2012, he provided two goals for W Connection en route to finishing runners-up in the 2012 CFU Club Championship and secure qualification for the Savonetta Boys in the 2012–13 CONCACAF Champions League. Following the season, Winchester had an unsuccessful one-week trial in Norway with FK Haugesund of the Tippeligaen. Shahdon opened the 2012–13 season as a starter for W Connection and made three consecutive appearances during the club's Champions League campaign. He later scored seven goals in as many matches in the Pro League, including his first career hat-trick as a professional on 5 January 2013 against Central FC. A week later, Shahdon flew to Jakobstad for a trial with Finnish club FF Jaro of the Veikkausliiga after agreeing to personal terms. Loan moves to FF Jaro (2013–2014) On