In the World Series ... 1932 and 1938 both of which were won by the Yankees in sweeps.
In the regular season ... 2003 when the Cubs won twice and the Yankees once and 2005 when the Yankees won all three games.
Prior to their meeting for three games on June 17-19, 2011 the Yankees lead the all time series 12-2.
Phil- Milwaukee Braves, Atlanta Braves, New York Yankees, Cleveland Indians and the Toronto Blue Jays. Joe- Chicago Cubs, San Diego Padres, Detroit Tigers, Atlanta Braves, Houston Astros, New York Yankees and Minnesota Twins.
Kevin Orie debuted on April 1, 1997, playing for the Chicago Cubs at Wrigley Field; he played his final game on September 26, 2002, playing for the Chicago Cubs at Wrigley Field.
Frank Fernandez debuted on September 12, 1967, playing for the New York Yankees at Yankee Stadium I; he played his final game on May 25, 1972, playing for the Chicago Cubs at Wrigley Field.
Al Shealy debuted on April 13, 1928, playing for the New York Yankees at Yankee Stadium I; he played his final game on September 3, 1930, playing for the Chicago Cubs at Wrigley Field.
Charlie Silvera debuted on September 29, 1948, playing for the New York Yankees at Yankee Stadium I; he played his final game on September 28, 1957, playing for the Chicago Cubs at Wrigley Field.
In MLB ... 1926-1937: New York Yankees 1938: Chicago Cubs 1939: Brooklyn Dodgers and New York Giants.
The Chicago Cubs play in Chicago, Illinois at Wrigley Field.The Chicago Cubs play their home games at Wrigley Field located in Chicago, Illinois.
Chicago Cubs from 1931-1938 New York Giants from 1939-1945 Chicago Cubs from 1946-1947
The Chicago Cubs play in Chicago, Illinois at Wrigley Field.The Chicago Cubs play their home games at Wrigley Field located in Chicago, Illinois.
New York, Chicago, and Los Angeles. New York Yankees New York Mets Chicago White Sox Chicago Cubs Los Angeles Dodgers Los Angeles Angels of Anaheim In reality, the Angels play in Anaheim not Los Angeles, although Anaheim is a suburb of L. A., it is a separate city.
Phil- Milwaukee Braves, Atlanta Braves, New York Yankees, Cleveland Indians and the Toronto Blue Jays. Joe- Chicago Cubs, San Diego Padres, Detroit Tigers, Atlanta Braves, Houston Astros, New York Yankees and Minnesota Twins.
The Chicago Cubs play their home games in Illinois.
Kevin Orie debuted on April 1, 1997, playing for the Chicago Cubs at Wrigley Field; he played his final game on September 26, 2002, playing for the Chicago Cubs at Wrigley Field.
Tony York debuted on April 18, 1944, playing for the Chicago Cubs at Wrigley Field; he played his final game on June 25, 1944, playing for the Chicago Cubs at Wrigley Field.
The Cubs of Chicago, IL play their home games in Wrigley Field in Chicago, IL.
The Yankees play in the Bronx, which is located in New York City, New York.
When the New York Yankees visit Chicago to play against the White Sox, they stay at the Hilton Chicago. It is located at 720 South Michigan Avenue in Downtown Chicago.