 Beginning with the 1995 playoffs , every playoffs have featured the Yankees and / or the Red Sox . As of 2012 , the two rivals have made up 25 out of 34 possible playoff appearances , with the two teams reaching the playoffs in the same year eight times ( 1995 , 1998 , 1999 , 2003 , 2004 , 2005 , 2007 , and 2009 ) . The streak ended in 2014 . 
