Kakitani was born in Osaka on January 3, 1990. He joined J1 League club Cerezo Osaka from their youth team in 2006. However Cerezo was relegated to J2 League end of the 2006 season. He played many matches from 2007. In June 2009, he moved to Tokushima Vortis on loan. He played as regular player until the 2011 season. In 2012, he returned to Cerezo which playing in J1. In 2013, he scored 21 goals and was selected Best Eleven award. In July 2014, he moved to Swiss Super League club Basel. In January 2016, he returned to Cerezo which playing in J2. Cerezo was promoted to J1 from 2017. In 2017, Cerezo won the champions in the J.League Cup and Emperor's Cup. In 2021, he moved to Nagoya Grampus.