The longest playoff losing streak in NFL history was during 2018-19 playoffs when the Kansas City Chiefs lost 12 of their last 14 playoff games .
As of the conclusion of the 2018–19 playoffs , they have lost 12 of their last 14 playoff games , including eight straight , at the time the longest playoff losing streak in NFL history , from the 1993-94 AFC Championship game to the 2013-14 Divisional Round and the only wins being a 30–0 win over the Texans in the 2015–16 playoffs and a 31–13 over the Colts in the 2018–19 playoffs.
Kansas City Chiefs