Darren Caldeira was part of the youth set-up at Mahindra United before going to Spain to train with La Liga side Valencia for a year. In 2010, he signed for Hero I-League side, Air India and played one season for them, later signing for Mumbai FC. Two years later, Bengaluru FC signed Caldeira and he spent two seasons there, after which he headed back to Mumbai FC in 2015. He was part of the Chennai City FC squad for the 2016-17 I-League season and a member of the ATK squad in the Hero ISL 2017-18 term. Caldeira last played for Mohun Bagan before making the move to the Kerala Blasters.
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