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Dawkins joined Tottenham Hotspur’s Academy in 2004. He featured in the reserves and was in the squad for UEFA Cup matches. He then left Spurs, going on trial at various clubs including Celtic, but re-joined the Lilywhites in 2011. He was then loaned out to the San Jose Earthquakes in the MLS. He then was put on loan to Aston Villa in the January transfer window of 2013. Following this he joined Derby County – he went on to make very impressive performances, which led to a permanent deal being agreed in 2014. After 2 years at Derby, he re-joined MLS side San Jose Earthquakes. He has represented the Jamaican National Team, with his debut on the 26th May 2014 against Serbia. He scored his first goal for his country in a 2-2 draw with Egypt.