 From 1920 through 2003 , the Yankees won 26 World Series championships and 39 pennants , compared to only four pennants for the Red Sox . In every year that the Red Sox won the pennant — 1946 , 1967 , 1975 and 1986 — they lost the World Series four games to three , leaving them with no World Series titles . During this time , the Red Sox finished second in the standings to the Yankees on twelve occasions — in 1938 , 1939 , 1941 , 1942 , 1949 , 1977 , 1978 , and every year from 1998 to 2003 . During the 84 @-@ year period , the Yankees finished with a better regular @-@ season record than the Red Sox 66 times , leading one sportswriter to quip that the Yankees ' rivalry with the Red Sox was much like the rivalry " between a hammer and a nail . " The Yankees finished second in the standings to the Red Sox twice , in 1986 and 1995 . 
