The 1999 New York Yankees season was the 97th season for the Bronx-based Major League Baseball team. The team finished with a record of 98–64 finishing 4 games ahead of the Boston Red Sox. New York was managed by Joe Torre. The Yankees played at Yankee Stadium. In the playoffs, they got to the World Series and defeated the Atlanta Braves in 4 games to win their 25th World Series title. By winning their 25th World Series, the New York Yankees became the most successful team in North America, a record previously held by the NHL's Montreal Canadiens. In that year, free-to-air broadcasts returned to WNYW, the which had been the first Yankees television broadcaster in 1947, while cable broadcasts continued on MSG.

Joseph Paul Torre is an American professional baseball executive, serving as a special assistant to the Commissioner of Baseball since 2020. He previously served in the capacity of Major League Baseball's (MLB) chief baseball officer from 2011 to 2020. He is also a former player, manager, and television color commentator. Torre ranks fifth all-time in MLB history with 2,326 wins as a manager. With 2,342 hits during his playing career, Torre is the only major leaguer to achieve both 2,000 hits as a player and 2,000 wins as a manager. From 1996 to 2007, he was the manager of the New York Yankees, and guided the team to six American League (AL) pennants and four World Series championships.