In 2010, Zaine Pierre joined TT Pro League club W Connection, went on trial with Stoke City, and made his debut for Trinidadian Club W Connection.
On 24 February 2010, he joined TT Pro League club W Connection. Earlier that month, Pierre had gone on trial with English team Stoke City. He made his debut for Trinidadian club W Connection on 20 September 2010. 
