Ainsley was born in Toronto, Ontario. Played with Trinidad and Tobago Under 20 National team in 2000. Then played NCAA Division l soccer at Canisius College in Buffalo, New York. After graduating in 2004, Ainsley played with Toronto Metro Lions, TV Badenstedt and the Orlando Sharks – while making brief stops with Hannover 96 ll and Kaiserslautern ll. In January, 2010 he graduated from Niagara University earning a Bachelor of Education degree. He has been teaching for the past 5 and half years. Ainsley also currently holds a U.S.S.F C licence with provisional status. He is also a youth soccer coach with Toronto Skillz Soccer Academy since 2008.