The Yankees longest streak of consecutive winning seasons was 39. It ran from 1926-1964.
the same team with 26 worls series titles . YAnkees! Yankees! Yankees! The Yankees just guaranteed (with their most recent win), a winning season for 2010. This ties the record for 2nd most consecutive winning seasons. The most consecutive winning seasons in MLB history: 1st - The New York Yankees: 1926 to 1964 (39 consecutive winning seasons) 2nd (tie) - Baltimore Orioles from 1968 to 1985 (18 consecutive winning seasons) - New York Yankees from 1993 to 2010 (18 consecutive winning seasons - streak still intact)
Dallas Cowboys. 20 consecutive winning seasons.
The New York Yankees have the record for longest consecutive winning season streak, at 39 years, from 1926 - 1964. The Yankees have also (2010 season) tied the second longest streak (NYY 1993 - 2010), shared by the Baltimore Orioles (1968 - 1985).
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Orioles and Yankees
The Chicago Cubs had winning seasons in 2007 (85-77) and 2008 (97-64), and as of this writing, stand one win away from 2009 being their third consecutive winning season. Before 2008, the Cubs had consecutive winning seasons in 2003 (88-74) and 2004 (89-73).In the time since the MLB season expanded to 162 games in 1962, the Cubs have had one other string of consecutive winning seasons: the six years from 1967 until 1972.Source: http://www.baseball-reference.com/teams/CHC/
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Yankees 54-62
The Dallas Cowboys from 1966 to 1985 (20 seasons) hold the record for most consecutive winning seasons.
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The Cowboys had a winning regular season record for 20 seasons between 1966-1985.