Winchester made his full international debut for the national team on 21 June 2010 against Antigua and Barbuda at the age of 18. He was later called up for three qualification matches for the 2010 Caribbean Cup, but only featured in a 4–0 win over Haiti. Shahdon did not receive a call-up with the national team again until June 2013, when he came on as a substitute in the "Soca Warriors"' friendly defeat away to Romania 4–0.