8. 2016 - 103-58-1 (.640)
Speaking of 71 years, the 2016 squad will forever be remembered by Cubs fans as the team that finally broke the ‘Curse’. The team set the record for most wins at Wrigley Field in a single season with 57. 2016 also featured career years from team staples Kris Bryant and Anthony Rizzo, both of whom finished top-five in MVP voting, with Bryant taking home the award. The 3-1 series comeback from Kris Bryant’s game-tying home run in Game 5 to Ben Zobrist’s go-ahead RBI double in Game 7 will go down in history as one of the greatest World Series of all time.
7. 1908 - 99-55-4 (.643)
After winning their first World Series the previous year, the Cubs wasted no time in recapturing their success. Their double-play combo of Joe Tinker, Johnny Evers, and Frank Chance all put up good offensive numbers, with Evers putting up a team-leading 143 OPS+. The real star of the team, however, was the starting pitching, namely that of Mordecai “Three Finger” Brown. Brown pitched to a 29-9 record with nine shutouts and a 1.47 ERA. In the World Series, Brown won Games 1 and 4, leading the Cubs to a five-game World Series win over the Detroit Tigers.