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On November 12, 2019, Inter Miami acquired Callender’s homegrown player rights from San Jose Earthquakes in return for the 27th overall choice in the 2020 Major League Soccer Draft and, if Callender achieves specific performance-based metrics, up to $150,000 in General Allocation Money.
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Prior to the club’s first Major League Soccer season in 2020, he was added to the roster. On May 7, 2021, Callender made his professional debut, starting for Inter Miami affiliate Fort Lauderdale CF in a USL League One matchup against Union Omaha.
Callendar was named to the league’s Team of the Matchday for week one after making six saves in Inter Miami’s 2023 season-opening victory over CF Montréal.
He scored a penalty and saved two to help his team, Inter Miami, win the first League Cup on August 19, 2023.
As a result, Drake Callender received Man of the Match and the 2023 Leagues Cup award for best goalie.