Windson made his first professional debut in 2002 acting in the TV series Moulmein High where he played the nerdy class geek, Chan Mun Kit. He was then selected by the TV station to represent the series to compete in the Best Actor category against the other Asian regions for a spot on the Asian Television Awards. Impressed by his performance in Moulmein High, Windson was then offered a role in the movie, After School by the movie’s producers. He was also part of Fugitives, the first Singaporean play to be performed in the newly opened Esplanade Theatre Studio in 2002. Windson then went on to graduate among the top of his drama school in 2004 and has since appeared in over 40 productions in 10 countries, with 7 cast recordings under his belt.
After which, armed with the continuing desire to further himself and the generous support of the National Arts Council Singapore, Windson moved to London and graduated with a Masters in Music Theatre from The Central School of Speech and Drama in 2010.
Windson’s UK credits include: Puss in Boots (Millfield Arts Centre) Chinglish (Park Theatre) Jack and the Beanstalk, Muncitor: All Workers Go to Heaven and Takeaway,(Theatre Royal Stratford East), Without Planning Permission (Fluxx), The Coffin is Too Big for the Hole (Platform 65), O Deptford, Nui Ah and Take Off. (Yellow Earth)
Windson was also the first Singaporean presenter to represent The Walt Disney Company as a host in The World of Disney XD, launching the channel, Disney XD, in Singapore.
Windson can be currently heard voicing Yin-Long in the latest season of Thomas and Friends and has appeared in the recent movie Philophobia.