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The Red Wings advanced to the Stanley Cup finals in 1941 and 1942, losing to the Boston Bruins and the Toronto Maple Leafs.

The Bruins swept the Red Wings in four games as Detroit was thwarted by the spectacular goaltending of goaltender Frank Brimsek, who lived up to his nickname of "Mr. Zero" by only allowing the Red Wings six goals in three series. The Red Wings won the first three games of the 1942 Stanley Cup Finals against the Maple Leafs, but Toronto rallied to win the next four and win the Cup. It was the first and only time a team has come back from a three games-to-none Cup finals deficit and only one of the two times in NHL history that a team has lost a playoff series after winning the first three games (the other occasion came when the Pittsburgh Penguins blew a 3-0 advantage against the New York Islanders in 1975).

But the Red Wings got their revenge on the Bruins and Brimsek by winning the third Stanley Cup in team history in a four game sweep of Boston in 1943. Detroit had also finished first overall with 61 points and a 25-14-11 record in 1942-43, the first season of the Original Six six-team NHL (the league had ranged from four-to-10 teams from it's beginning in 1917-18 until 1941-42).

That season began what has become known as the NHL's "Golden Age", which lasted through the 1966-67 season, after which the league doubled in size to 12 teams.

The 1944 season saw an offensive explosion in the NHL as many of the league's best, and defensive players were serving in World War II (both Sid Abel and Jack Stewart served in the Royal Canadian air Force in 1943-44 and 1944-45). The NHL's leading scorer, Boston's Herb Cain, had 36 goals and 82 points and the Red Wings Carl Liscombe finished fourth in the scoring race with a team record 36 goals, 37 assists and 73 points.

Detroit wouldn't capture the Stanley Cup again until 1950, but the late '40s would see the arrival of a group of players who would become not only Red Wing legends, but the makings of NHL lore.

With the promotions of Ted Lindsay (1944-45), Gordie Howe (1946-47), Red Kelly (1947-48) and Terry Sawchuk (1949-50) to the NHL and the return of both Abel and Stewart from the RCAF, one of the greatest dynasties in NHL history was set in motion. Adams handed the coaching reins to Tommy Ivan after the 1946-47 season. Detroit finished second overall during the 1947-48 regular season, five points behind the Toronto Maple Leafs. But the team then ran off a streak of seven-straight first overall finishes from 1948-49 until 1954-55 and won four Stanley Cups (1950, 1952, 1954 and 1955).