professional debut for the Sharks in a loss to Caledonia AIA. However, after the arrival of Antiguan Peter Byers the next month, 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. Winchester finished his first season with Central FC with a goal in the semifinals of the Digicel Pro Bowl against North East Stars. 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. 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. On 13 September 2013, Rundell opened the Pro League season with a goal in a 3–1 win over Pro League defending champions Defence Force. His strong start to the season was ultimately rewarded with a call-up to the national team. In October 2013, Winchester was named the most valuable player of the First Citizens Cup after scoring the winning goal to give Central FC its first major trophy in a 2–1 win over Defence Force in the final. Four days later, he recorded his first career hat-trick as a professional on 22 October against Point Fortin Civic. After his successful month, Winchester was named Pro League Player of the Month for October. Winchester concluded his second season with Central FC by leading the Sharks to the 2014 Goal Shield over rivals W Connection and winning his second most valuable player award of the season. Following the season, Winchester signed a two-year contract extension, keeping him with Central FC until the end of the 2015–16 season. On 17 July 2014, Winchester traveled to Visé to discuss personal terms with Belgian club C.S. Visé. Prior to departing for Belgium, Winchester recorded nine goals in the TT Pro League and 18 goals in all competitions in his two years with Central. Cercle Sportif Visé On 22 July 2014, Winchester agreed to join C.S. Visé of the Belgian Third Division on a free transfer from Central FC and was reunited with former manager Terry Fenwick and teammate Willis Plaza. PS Kemi On 12 May 2016, Winchester signed a deal with PS Kemi that would see him awarded a one-year