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Crowley first played Gaelic football at juvenile and underage levels with Castlehaven before joining the club's senior team as a 17-year-old. His performances in these grades resulted in his inclusion on the Cork minor and under-21 teams. Crowley enjoyed his first major club success when Castlehaven won the Munster Club Championship in 1997. He won a County Under-21 Championship medal the following year. Crowley joined the Cork senior football team in 2002 and won a Munster Championship medal in his debut year. He won a County Senior Championship title with Castlehaven in 2003, a victory which resulted in him taking over the captaincy of the Cork senior team in 2004.