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Toronto Maple Leafs' Phil Kessel (L) is congratulated by teammates Ryan Hamilton (C) and Nazem Kadri after Kessel scored a goal against the Boston Bruins in the third period of Game 2 of their NHL Eastern Conference Quarterfinal playoff series in Boston, Massachusetts May 4, 2013.BRIAN SNYDER/Reuters

For the past nine years, Adam Savel has slept under his Toronto Maple Leafs blanket, dreaming the impossible dream.

"I sleep with it every night," said Mr. Savel, a strapping 26-year-old man, without a trace of embarrassment. "On the ten-scale of fans, I'm an 11.5."

His dream – and that of countless other fans whose happiness hinges on the fortunes of the Maple Leafs – is set to become reality Monday night, when Toronto plays host to its first playoff game since May 4, 2004.

Across the city – and well beyond its borders – fans will converge on the Air Canada Centre, sports bars and living rooms to witness the team attempt to take a 2-1 series lead against the Boston Bruins. Mayor Rob Ford issued a proclamation declaring Monday as "Blue and White Day," encouraging Torontonians to sport the team's colours.

The game will test the mettle of a fan base that is relentlessly faithful, if spiritually battered, from decades of failure.

Having endured an endless loop of disappointment since the Maple Leafs last won the Stanley Cup in 1967, older fans have learned to keep their emotions in check; approaching the game with a mix of excitement and fear.

"I can't even watch these games," said Jim McMillan, 53. "We have gotten so used to losing. You just anticipate disaster."

For a younger, less jaundiced generation of fans, however, there is the thrill of a brand of hockey that outstrips the regular season.

Their hopes were temporarily dashed after Game One of the series, when the Bruins ground the Leafs into the ice at TD Garden. However, a 4-2 victory for the Leafs in Game Two rekindled their confidence.

"I'm not really a hockey fan, but I want to witness history," said Junior Patel, 21, downing beer with friends Sunday afternoon at a Toronto sports bar.

Ishaun Khosla, a University of Western Ontario student, said that he was so buoyed by Game Two that he went online to order a Leafs jersey. "This is really going to bring the city together," predicted Mr. Khosla, 25.

Tickets to Monday's game are out of reach for many, and prices are being driven steadily higher, said Rob Pakulski, owner of Crown Tickets, a ticket-scalping operation. He said that poor seats are going for about $300. The best seats fetch up to $750.

A high proportion of his customers are keen on taking their grandchildren to see a team they recall through the mists of time as being a thrilling, perennial winner, said Mr. Pakulski.

"They have experienced how unbelievable a playoff game is," he said. "The vibe is just crazy. People I haven't heard from in ten years are searching their homes for their old Leaf jerseys and calling me for tickets."

Mr. Pakulski conceded that he is no less affected than his customers. "I'm a Leaf victim, just like the rest," he said. "Like the rest of the victims, I've been saying 'maybe next year,' since 1968."

And should the Leafs manage to vanquish Boston and make it to the next playoff round, even non-believers will find it impossible to remain aloof, said 24-year-old Pranshu Bharadwaj.

"I don't want to sound like a bandwagon jumper, but even I know this is a big deal," said Mr. Bharadwaj, whose first love is basketball. "If they win this game, I'm going to start watching with more focus. And if they win the series, I'm jumping on board."

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