But with 19 games left to play, Toronto is in great position to finally end that drought. They sit seventh in the Eastern Conference with 62 points, four points clear of ninth-place Washington (though the Caps have a game in hand).
The playoffs are by no means a lock at this point, but GM Brian Burke has an opportunity to strike a deadline deal that will push the Leafs further up the standings. They are six points behind the Northeast Division-leading Bruins and probably won't catch them, but fourth place and a home playoff series are only six points out of their reach.
The Leafs most glaring problem might be the hardest to fix, especially in season - goaltending. The combination of James Reimer and Jonas Gustavsson have been serviceable for this team, but their 155 goals allowed puts them in the bottom half of the league despite one of the better defensive corps in hockey.
Gustavsson is an unrestricted free agent next year, and the Leafs could choose to add a goalie and let him walk, or flip him as part of a deal to upgrade at the position.
Schneider, the 2009 American Hockey League goaltender of the year, is a restricted free agent, so the Canucks aren't quite as motivated to move him as they might otherwise be. But if they want to strike while he has maximum value, this might be the time.
Asking price on Schneider is expected to be high as potential franchise goaltenders don't come cheap, but if the Leafs are willing to part with some picks (like they did to acquire Phil Kessel) or perhaps a prospect like Joe Colborne, they can get it done.
St. Louis could also be motivated to get rid of AHL All Star game Most Valuable Player Ben Bishop as he is an unrestricted free agent at the end of the year. But the 6'6 netminder is far less proven at the NHL level than Schneider and might not be an upgrade over what Toronto has on its roster now.
Up front, the Maple Leafs could use much more depth on the left side. Joffrey Lupul is a world-beater and Clarke MacArthur is a great second or third line player but the talent drops off a cliff after those two.
Tuomo Ruutu of the Carolina Hurricanes fits their needs perfectly - the question is can Burke put together a package to get him. He is the top available commodity by general consensus and last year's best available player, Thomas Kaberle, went to Boston for Colborne as well as a first and second round pick.
On the other hand, the Leafs are surging right now without any help. They have won six of their last eight games and three of four since the All Star break. They leapfrogged the hated Senators with a win last night and appear to be a team that is destined for the playoffs as currently constituted.
It remains to be seen if Burke can make anything happen, but as he is one of the smartest and most experienced general managers in the league Leafs fans can feel as though their pride and joy is in safe hands.