6 times in 30 years

[sdog1981]

At least the Niners made it to a Super Bowl in 2013. Can't say that about the Almighty Cowboys.

There's several other teams that deserve mention as having suffered through a lot of recent losing, including the Jets, Dolphins, Raiders, and Bengals.

The Bengals are on a completely different level of losing and woe. Since 1968 the Bengals have had 10 head coaches and only three of them have a winning record.