The 1999 World Series, the 95th edition of Major League Baseball's championship series, featured a match between the defending champions New York Yankees of the American League against the Atlanta Braves of the National League. This was a rematch of the 1996 World Series where the Yankees defeated the Braves as well. Held during the month of October, the Yankees swept the Series in four games for their second consecutive title, third in four years, and 25th overall. This was also their second World Series appearance in a four-year span (1998–2001). It is remembered for Chad Curtis' home run in Game 3, which gave the Yankees a 6–5 victory and Game 2, featuring Jim Gray of NBC's infamous interview with Pete Rose.

The New York Yankees won their second straight World Series, and beat the Braves franchise for the third consecutive time (having defeated the Milwaukee Braves in their 1958 Series).

The 1999 World Series also featured the All-Century Team, featuring the greatest players of the Twentieth Century voted by both the fans and sportswriters. One of the players on the All-Century Team, Yankee legend Joe DiMaggio, had died in March of that year, causing the Yankees to honor him by wearing a black #5 on their sleeves.

This featured a rematch of the 1996 World Series. It would also be the last World Series until 2013 in which the two teams with the best regular-season records in their respective leagues would face off. Perhaps most significantly, it was the first World Series ever in which the competing teams had played each other in the regular season. Although interleague play had begun in 1997, neither the 1997 nor 1998 series saw a rematch from the regular season.

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