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As of October 2023, Tony La Russa has a win-loss record of 1,025 wins and 1,069 losses against the Chicago Cubs during his managerial career. This record reflects his time managing both the Chicago White Sox and the St. Louis Cardinals, where he faced the Cubs numerous times. La Russa is known for his strategic approach to the game, which has contributed to his overall successful managerial career despite the competitive rivalry with the Cubs.

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