The New York Yankees have won the World Series 27 times, which is the most championships won by any team in Major League Baseball history. Their titles span from their first win in 1923 through to their most recent championship in 2009. The Yankees hold many records, including winning the World Series five times in a row from 1949 to 1953 and four times in a row from 1936 to 1939. They have appeared in 41 World Series overall.