Theodore Whitmore was born on 5 August 1972 in Montego Bay, Jamaica. He started his professional football career in Montego Bay Boys Club. In 1994 he joined Violet Kickers, but later moved to Seba United. In 1999 Whitmore was signed by the English club Hull City and made 77 appearances for the team and scored 9 goals. Later he moved to Scottish club Livingston, yet finished his career in 2006 in Jamaican side Seba United.
Whitmore made 105 appearances for the national side and scored 24 goals.
His coaching career started in 2006 when he was appointed as a boss of Seba United. Soon afterwards Whitmore took over the post of the interim national team coach and in 2009 he was confirmed at the post and lead the team to 2010 Digicel Cup victory.
Failing to provide a solid competition for during the 2014 qualifiers, Whitmore was released from his job in the summer 2013.
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