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Flamengo was the club Jorge Jesus managed after his first stint with Benfica. He left Benfica in 2019 and joined Flamengo in June of the same year. During his time with Flamengo, Jesus led the team to several titles, including the Campeonato Brasileiro Série A, the Copa Libertadores, and the Recopa Sudamericana. He left Flamengo in 2020 and returned to Benfica in 2021.