Firstly, this entry is about NHL, NBA, NFL and MLB championships. I realize Toronto has had great success in lacrosse and has won Grey Cups recently, but with all due respect, I'm not counting them as major championships. For Toronto, I'm only counting the Maple Leafs, Blue Jays and Raptors.
That means Toronto hasn't won a championship since 1993. That's a 22 year drought. As bad as that sounds, many cities have it worse.
Let's start with San Diego. The Chargers haven't won since 1963, the Padres have never won a World Series, and even their former NBA teams (Rockets and Clippers) didn't win a thing.
52 year drought
I'm rooting heavily for the Cavaliers in this year's NBA championship and they're currently tied 1-1 with the Warriors. The Cavs have never won a title, the Indians haven't won since 1948 and the Browns haven't won since 1964.
51 year drought
Buffalo only has the two teams, but that's enough to count. The Sabres have never won a Stanley Cup and the Bills haven't won since 1965.
50 year drought
Kansas City also only has two teams, but they did have a short-lived NHL and NBA franchise. Neither won a thing. The Chiefs haven't won the Super Bowl since 1970 and the Royals haven't won a World Series since 1985.
30 year drought
The Golden State Warriors haven't won since 1975, the Oakland Raiders haven't won since 1983, and the A's haven't won since 1989.
26 year drought
The Bengals have been consistently brutal throughout the years, never winning a title. Meanwhile, the Reds haven't won a World Series since 1990.
25 year drought
The Vikings have never won a Super Bowl, the North Stars and Wild have never won a Stanley Cup, the Timberwolves have never won and the Twins haven't won a World Series since 1991.
24 year drought
The Bullets / Wizards haven't won since 1978, the Capitals have never won, the Nationals have never won and their NFL franchise hasn't won a Super Bowl since 1992.
23 year drought