Maddon managed the Chicago Cubs from 2015 to 2019, breaking the Cubs' 108-year World Series Championship drought in his second year with a 4–3 series win over the Cleveland Indians. His .581 winning percentage is the most for a Cubs manager since Frank Chance, and his 19 playoff victories as manager are a team record, as are the team's four consecutive playoff berths from 2015 to 2018. Following the Cubs quick exit from the 2018 playoffs, the Cubs opted not to extend Maddon an extension on his five-year contract, which the team allowed to expire after Chicago failed to make the playoffs the following year.