There are many cities that have won 2 in the same year, Detroit did it fairly recently with the NBA and NHL.
I was curious as to what city was the closest to winning all 4 championships in a single year, or have had all 4 sports teams make it to the finals in the same year.
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While not all in the same calendar year, Detroit won three major sports championships in a 6 month span in the mid 30s (prior to the NBA), making it the only city to win 'all' major pro sports championships within a one year period, and earning the nickname 'The City of Champions'.
The Tigers won the World Series on 10-7-1935
The Lions won the NFL Championship Game on 12-15-1935
The Red Wings won the Stanley Cup on 4-11-1936
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A more recent similar example is New York in 1969-1970, though not within a one year period.
The Jets won the Super Bowl in January 1969
The Miracle Mets won the World Series in October 1969
The NY Knicks won the NBA in April 1970
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In January 1981, the Philadelphia Eagles lost the Super Bowl to the Oakland Raiders. In 1980, the Phillies won the World Series for the first time, the 76ers lost to the Lakers in the NBA Finals, and the Flyers were defeated by the Islanders; this was the only time in history that one city had competed for the championships in all 4 major sports within one year's time (had the three losing teams won, Philadelphia would have held defending championships in the NFL, MLB, NBA, and NHL).
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If one limits to major sports: Football - NFL/AFL and Canadian Football League Hockey - NHL/AHL Baseball - MLB Basketball - NBA, ABA then we have ten cities since 1927. Most of the data is from Bill on Yahoo Answers. URL at http://answers.yahoo.com/question/index?qid=20070606002545AAX4LiE New York - 7 times, Detroit, Pittsburgh, and Toronto - 2 each Baltimore, Boston, Chicago, Edmonton, Oakland, and Montreal - 1 each List by Year: 2008-09 Pittsburgh Steelers, Pittsburgh Penguins 2004-05 Boston Red Sox, New England Patriots
1987-88 Edmonton Oilers, Edmonton Eskimos
1986-87 New York Mets, New York Giants
1981-82 Los Angeles Dodgers, Los Angeles Lakers
1979-80 Pittsburgh Pirates, Pittsburgh Steelers
1977-78 Montreal Canadiens, Montreal Alouettes
1974-75 Oakland Athletics, Golden State Warriors
1970-71 Baltimore Orioles, Baltimore Colts
1969-70 New York Mets, New York Knicks
1956-57 New York Giants, New York Yankees
1953-54 Detroit Red Wings, Detroit Lions
1947-48 Toronto Maple Leafs, Toronto Argonauts
1946-47 Toronto Maple Leafs, Toronto Argonauts
1939-40 New York Rangers, New York Yankees
1938-39 New York Giants, New York Yankees
1935-36 Detroit Lions, Detroit Red Wings, Detroit Tigers
1933-34 Chicago Bears, Chicago Blackhawks
1932-33 New York Rangers, New York Yankees
1927-28 New York Giants, New York Rangers, New York Yankees
It has happened in three calendar years:
1969 -- The New York Jets won Super Bowl III in January; the New York Mets won the World Series in October.
1979 -- The Pittsburgh Steelers won Super Bowl XIII in January; the Pittsburgh Pirates won the World Series in October.
2004 -- The New England Patriots won Super Bowl XXXVIII in January; the Boston Red Sox won the World Series in October.