Savonetta Boys to a runners-up finish with three goals in four matches during the 2015 CFU Club Championship and qualify for the following season's Champions League. Winchester started the 2015–16 season with W Connection, changed from the number 16 jersey in favour of number 9, and was named a vice-captain. In the 2015–16 CONCACAF Champions League, he made two appearances against Santos Laguna and Saprissa during W Connection's group stage matches. Afterwards, Winchester provided four goals during the First Citizens Cup and TOYOTA Classic en route to W Connection claiming both crowns. In Pro League competition, Winchester scored a further seven goals during the first half of the season — tying his most Pro League goals in a season. On 24 February 2016, Winchester received his first career red card and an automatic two match suspension for retaliation following a punch from Atlántico FC's Mateo Zazo during the Savonetta Boys CFU Club Championship opening match. Shahdon returned to score a goal against Arnett Gardens in the semifinals to help W Connection qualify for its second consecutive Champions League. However, he received another red card for a reckless challenge in the first half of a 3–0 loss to Couva rivals Central FC in the final. Murciélagos On 22 June 2016, Winchester signed along with former W Connection and international teammate Jomal Williams with Mexican club Murciélagos of Ascenso MX prior to the start of the 2016 Apertura for an undisclosed transfer. Kapaz (loan) On 8 February 2018, Winchester signed for Kapaz PFK on loan from Murciélagos F.C. until the end of the 2017/18 season. SJK After his Murciélagos' contract expired in July 2018, Winchester was unveiled as a new signing for SJK on 26 July 2018. SJK announced that Winchester had left the club on 30 November 2018. International career Winchester represented Trinidad and Tobago on various levels of international competition, having been capped for the under-17, under-20, under-23 Olympic team, and the Trinidad and Tobago national teams. Youth teams He began his international career for the under-17 team during the Soca Warriors''' runners-up finish in the 2008 CFU Youth Cup. During the competition, Winchester made five appearances and scored a pair of goals against Aruba. In April 2009, Winchester made three starts during the 2009 CONCACAF U-17 Championship, which witnessed the team eliminated without scoring a goal. In November 2010, Winchester scored three goals in four matches to lead the