Going into the 2012 season, the Cowboys had a .500 or better record from 1965 to 1985. Then losing records from 1986 to 1990. Winning records again from 1991 to 1996, then a losing record in 1997. 1998 winning record, 1999 .500 record. Losing records from 2000 to 2002, winning record in 2003 and losing record in 2004. They had a winning record from 2005 to 2009. The Cowboys best run was 26 seasons in a row.
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On January 4, 2015, the Dallas Cowboys defeated the Detroit Lions, 24-20, in a wild-card playoff game at AT&T Stadium in Arlington, Texas. Cowboys quarterback Tony Romo, whose postseason record as a starter is 2-3, threw for two touchdowns and 293 yards in the contest.
Thirteen seasons. The Cowboys' 34-14 playoff win over the Philadelphia Eagles on January 9, 2010 was their first since they defeated the Minnesota Vikings 40-15 on December 28, 1996.
The Cowboys' latest playoff win was a 24-20 win over the Detroit Lions in a wild-card round contest at AT&T Stadium on January 4, 2015.
Through the 2017 season, the Cowboys have losing records against the Baltimore Ravens (1-4), the Cleveland Browns (14-17), the Denver Broncos (5-8) and the Green Bay Packers (17-19)).
From 1901-2012, the Detroit Tigers have had 44 losing seasons.
As of November 15, 2009, they are 1-6 against the Green Bay Packers at Lambeau. After "breaking the jinx" for their first Lambeau win on September 21, 2008, the Cowboys suffered a reversal of fortunes on November 15, 2009, losing to the Packers 17-7.(see the related link)
Pittsburgh pirates 19 seasons
The UPS guy asked me this and seems to think my beloved Cardinals is the team with only 2 consecutive losing seasons in the last 30 or 40 years but hopefully someone can confirm and explain. When you google it only seems to correlate losing with most. ---- The Cardinals had consecutive losing seasons in 1994 (53-61) and 1995 (62-81). Prior to that their last consecutive losing seasons came in 1958 and 1959. Since the 1960 season, the Cardinals are the only MLB team to have one set of consecutive losing seasons. The Los Angeles Dodgers have had two sets of consecutive losing seasons since 1960 (1967-1968 and 1986-1987).