A Mahindra United youth academy product, Darren spent a year at Valencia CF training with the U-18 team.
In 2010, after the dissolution of Mahindra United, he signed with Air India FC before moving to Mumbai FC in 2011. After a couple of seasons at Mumbai, Caldeira was on the move again and signed with new I-League entrants Bengaluru FC in July 2013 and helped them win the league.
Darren switched back to Mumbai FC in 2015 before briefly appearing for Bengaluru FC for a few months in 2016.
Then Chennai City FC who were again new entrants to the I-League signed the midfielder in January of 2017. After making nine appearances for the club, Caldeira moved to ATK for the 2017-18 season, but he only ended up making three appearances for the Kolkata side.
Last season, Darren was at Mohun Bagan and cumulatively between the I-League and the Calcutta Football League featured 13 times for the Mariners.
I’m delighted to be wearing yellow this season.
It is a great time to be part of a club that has a clear set of objectives they wish to achieve with an accomplished coach and a new set of players.Darren Caldeira
Darren is a very consistent and stable player who can play all over the midfield. His experience with several ISL and I-league clubs will surely be an asset to the team.
Moreover, he has proven to be a team-player with a great attitude.Eelco Schattorie, Head Coach, Kerala Blasters FC