World Series World Series Titles Franchise Records Yankees Legacy 2020 vs 2024 Titles World Series Champions Yankees' Drought 1969 World Series Toronto Blue Jays Titles 1985 and 2015 2000 Yankees 1985 and 2015 World Series Yankees Dynasty High School Championships Franchise Successes Notable Matches Participation Records 1995 Championship 1995 Championship Ring 2004 Red Sox Championship Winning Teams Franchise Success