No team has won more World Series titles than the New York Yankees have (27). The first was claimed in 1923, a six-game win over the New York Giants. The 27th was another six-game affair, this time a victory over the Philadelphia Phillies. That occurred in 2009. The team has not played in a World Series since, losing in the ALCS on four occasions in that period, in 2010, 2012, 2017 and 2019.