This list is sort of a companion/alternate to the "losingest cities" list. This focusses more on playoff disaster rather than regular season records.
From Forbes Magazine description
How to figure which fans have endured the most pain? To start, we checked the records of those teams that have performed worst in the World Series, Super Bowl (or NFL and AFL title games before the Super Sunday era), NBA (and ABA) finals and NHL Stanley Cup finals.
Next, we looked at records of teams one round earlier, compiling a list of ball clubs with the worst success rate in each sport's semifinal rounds over the years, followed by those performing the poorest in earlier playoff rounds. (Second place finishes in baseball count in this round, given the sport's low number of playoff teams. Who can forget the those tough pennant races like the Red Sox 1978 loss to the Yankees on Bucky Dent's homer in a one-game tie breaker or the Phillies' famous 1964 collapse, when they blew a six-and-a-half game National League lead with 12 games to play?).
To give the pure championship drought factor a voice, we gave some weight to each city's ratio of total seasons (all four sports combined) to championships. And since few things can break fans' hearts more than seeing their team pack up and move--just ask former rooters of the Dodgers, original Cleveland Browns or Baltimore Colts--cities whose fans were abandoned were awarded heartbreak bonus points.
We limited the study to cities with at least 75 cumulative football, basketball, baseball and hockey seasons, including older franchises that have since moved on, like the Philadelphia (now Golden State) Warriors and Cleveland (now St. Louis, via Los Angeles) Rams. And figuring no fan who has seen his team win a championship in the past five years could be too heart broken, we eliminated those cities that have produced at least one title since 2003.
5 =
Apocalyptic