Which NFL teams have the worst post-season record over the last 25 years?
It all started so well for Dallas at the beginning of the Jerry Jones era but now the Cowboys and the Lions hold an unwanted playoffs record.

The Dallas Cowboys and the Detroit Lions are two of the most important franchises in the NFL. The former are one on the most successful teams in the Super Bowl era, with five wins to their name, while the latter are one of the oldest franchises in league history, joining the NFL in 1930 before moving to Detroit and rebranding as the Lions in 1934. However, both the Cowboys and the Lions have fallen on lean times in terms of playoff success over the last 25 years.
Over the course of the past quarter century, Dallas and Detroit have the worst post-season records in the NFL, with a playoff victory percentage of lower than .250.
Jerry Jones and drought in Dallas
When Jerry Jones assumed control of the Cowboys in 1989 and brought in Troy Aikman with the first draft pick it heralded an era of success that reaped Super Bowl championships in 1992, 1993 and 1995 and a run of six consecutive playoffs appearances from 1991 to 1996.
However, since 1997, the Cowboys have only made the post-season on 10 occasions, playing 13 games with a record of 3-10, a win percentage of .237. Dallas’ three wins all came in the wild card round, against the Eagles (2009), Lions (2014) and Seahawks (2018). Their most regular tormenters have been the Packers and the Vikings, who have both beaten the Cowboys twice in post-season over that period.

Lions tamed in wild card round
The case of the Lions is even more paradigmatic. In the last 25 years they have made only five post-season appearances and have not made it beyond the regular season since 2016.
The Lions have been beaten in the wild card round each time they have progressed to the playoffs over the timeframe, losing to the Buccaneers, the Commanders, the Saints, the Cowboys and the Seahawks) for win percentage of .000.
Overall, the Lions’ winless streak in the playoffs stretches back to 1993: their last post-season victory came against the Cowboys in 1991.