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Cherundolo joined Hannover 96 in 1998, marking the beginning of his successful career with the German club. He quickly established himself as a key player in the team's defense, earning recognition for his athleticism, tackling ability, and composure on the ball. Cherundolo's contributions helped Hannover 96 achieve notable results, including winning the DFB-Pokal in 1999 and securing a UEFA Champions League berth in 2000.