For longtime Toronto sports fans, Monday’s heartbreaking 5-4 overtime loss by the Maple Leafs to the Boston Bruins brought back memories of other crushing disappointments in Toronto. Here are five of the most memorable sporting heartbreaks:

The Disaster in Detroit: The 1987 Blue Jays were within grasp of the American League East Division title in the last week of the season, up 3 ½ games with seven left to play. The Jays lost an astounding seven games in a row to watch their playoff hopes dissolve, falling to the Detroit Tigers on Oct. 4, the last day of the season. It was the lowest of lows, third basemen Garth Iorg wrote in a column for the Star. Outfielder George Bell said he wished he could fly away to the Dominican and disappear from the reality of the stunning collapse. “I don’t want to think about baseball any more now,” he said.

Leafs lose to Kings in 1993 playoffs: A Maple Leafs win against the Los Angeles Kings in the 1992-93 playoffs would have set up a dream Stanley Cup final between Toronto and storied rival Montreal Canadiens. The Leafs were up 3-2 in the series but lost Game 6 in Los Angeles in overtime. Now part of Toronto sporting lore, Wayne Gretzky high-sticked Leafs captain Doug Gilmour in OT, drawing blood, but wasn’t penalized by referee Kerry Fraser. Gretzky then scored the winning goal moments later. The series then went to a decisive Game 7 at Maple Leaf Gardens. Some say it was Gretzky’s best game of his legendary career. He scored a hat trick, carrying his Kings to a 5-4 win over the team he grew up cheering for. Twenty years later, that series is still seen by some as the best recent chance the Leafs had to go all the way and win a Cup.

Vince Carter’s missed basket: The Raptors were a buzzer beater away from advancing to the Eastern Conference finals in 2001. The Raptors trailed by one point to the Philadelphia 76ers and with two seconds left, Vince Carter hoisted a shot from about 19 feet out that hit the rim and bounced out. “It didn’t go in. It’s that simple,” Carter said after the game. “I had the opportunity, and it just didn’t fall.” That Game 7 was the furthest the Raptors franchise have gone in the playoffs. They haven’t won a playoff series since 2001, and haven’t made the playoffs since 2008.

Losing the 2008 Olympics: The vision was grand — a Toronto Summer Olympics would transform the city and draw crowds to its waterfront. So grand was the vision that thousands of people cheered on the streets of downtown Toronto in support of the bid, awaiting the announcement. The disappointment was hard to swallow in 2001, when the International Olympic Committee chose Beijing to host the 2008 Olympics instead. Beijing garnered 56 votes, while Toronto came in a very distant second, with only 22 votes. So much for a party in the streets.

Leon McQuay’s fumble: McQuay fumbled the ball at the 11-yard-line with less than two minutes to play against Calgary in the 1971 Grey Cup, costing the Argos a chance to tie the game. The Argos went on to lose 14-11. Some blame the new and slippery artificial turf at Empire Stadium in B.C. Others say the Argos had no chance at winning even if it he tied the game. No matter what caused him to slip, it went down as one of the most storied miscues in CFL history.

What do you think?

Read more about: