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Toronto Maple Leafs (NHL, 1987-88)

1987-88 Stanley Cup Playoffs: Maple Leafs vs. Detroit Red Wings      To say the least, the 1980s were the "dark ages" for the Toronto Maple Leafs. The last decade of the Harold Ballard ownership era saw the Leafs fail to advance past the second round of the playoffs and never finish over .500. The team would have talented players here and there (Wendel Clark, Russ Courtnall, Rick Vaive, to name a few) but would have little else throughout the roster, due to front office incompetence. In numerous cases, the Leafs would have a miserable season, but stagger into the postseason due to the NHL's playoff format that saw 16 of the 21 teams qualify.      Case in point, the 1987-88 edition of the "Maple Laughs". After advancing to Game 7 of the second round for two straight seasons, it appeared the Leafs were on the rise. Of course, that did not happen, as the Leafs, led by fiery head coach John Brophy, had a truly awful season. "Brophy's Boys" finishe...

Toronto Maple Leafs (NHL, 1994-95)

1994-95 Regular Season, Opponent Unknown      The Toronto Maple Leafs were coming off back-to-back trips to the Western Conference Finals in 1993 and 1994, resurrecting a franchise that had been mostly a bottom-feeder throughout the 1980s and early 1990s. The 1994-95 season started late due to a lockout, and was shortened to 48 games and not starting until January.      After that second straight conference finals loss, GM Cliff Fletcher shook up the roster. Fletcher dealt longtime Leafs captain Wendel Clark to Quebec for Mats Sundin, a young forward in just his fifth season. While a shocking trade at the time (Clark had just had a career year), the Leafs made out like bandits in the long run, as Sundin spent the next 14 years of his career in Toronto.      The Leafs stumbled in 1994-95, dropping to fourth place in the Central Division, with a mediocre 21-19-8 record. The team hovered around the .500 mark all year, but was still able to...

Toronto Maple Leafs (NHL, 1998-99)

1998-99 Regular Season: Leafs vs. Chicago Blackhawks      1998-99 was a memorable season for the Toronto Maple Leafs. Maple Leaf Gardens, the Leafs iconic home for the past 68 years, was closing midway through the year, replaced by the Air Canada Center.      Since it's grand opening in 1931, the Gardens had been home to not only the Leafs, but also pro basketball, pro wrestling, rock concerts, boxing, you name it. It saw the highs of 11 Stanley Cup championships to the nadir of the Harold Ballard era of the 1970s and 1980s. The building had become not just a legendary sports arena, but a Canadian cultural shrine.      The Maple Leafs were coming off two straight disappointing seasons by the time 1998-99 rolled around. The team had slumped after making two straight conference finals in the early 1990s, and missed the playoffs altogether in 1997 and 1998.       Major changes were made for the upco...