1999
- January 12
- Setting an all-time record, Mark McGwire's 70th home run ball in one season is purchased at an auction by an anonymous buyer for $3 million. [56]
- January 13
- After 13 years of playing NBA basketball, superstar Michael Jordan announces his second retirement from basketball. [20]
- January 31
- NFL Super Bowl XXXIII: Denver Broncos beat Atlanta Falcons in Miami, Florida; Most Valuable Player: John Elway, Denver, Quarterback. [1]
- Death of Norm Zauchin, baseball player (born 1929). [20]
- March 8
- Death of Joe DiMaggio, baseball player (born 1914). [20]
- March 24
- Death of Birdie Tebbetts, baseball player and manager (born 1912). [20]
- March 25
- Death of Cal Ripken, Sr., baseball player and manager (born 1935). [20]
- March 27
- Death of Nahum Stelmach, football player (born 1936). [20]
- March 28
- 18th NCAA Women's Basketball Championship: Purdue beats Duke 62-45 in San Jose California. [1]
- March 29
- UConn defeats Duke 77-74, for the 61st NCAA Men's Division I Basketball Championship. [1] [20]
- April 11
- 63rd Golf Masters Championship. [1]
- April 18
- "The Great One" Wayne Gretzky plays his final National Hockey League game. [20]
- April 20
- Death of Richard Rood, American professional wrestler (born 1958). [20]
- April 25
- Death of Lord Killanin, Irish journalist and president of the International Olympic Committee (born 1914). [20]
- April 30
- Death of Sir Alf Ramsey, 1966 England World Cup winning football manager (born 1920). [20]
- May 1
- 125th Kentucky Derby: Chris Antley aboard Charismatic wins in 2:03.2. [1]
- May 3
- Death of Steve Chiasson, Canadian hockey player (born 1967). [20]
- May 7
- The Cleveland Indians score 18 runs in the final three innings to overcome a 9-1 deficit to beat the Tampa Bay Devil Rays, 20-11. [56]
- May 8
- Jimmy Glass scores the goal that keeps Carlisle United in the Football League. [20]
- May 15
- 125th Preakness: Chris Antley on Charismatic wins in 1:55.2. [1]
- May 18
- Death of Betty Robinson, American athlete (born 1911). [20]
- May 23
- Death of Owen Hart, Canadian professional wrestler (born 1965). [20]
- May 26
- Manchester United wins the UEFA Champions League at the Nou Camp stadium, Barcelona, beating Bayern Munich to lift their third major trophy of the season, after winning the English Premier League and FA Cup, an unprecedented feat for a single season. [20]
- June 16
- Sociedade Esportiva Palmeiras wins the Libertadores Cup. [20]
- June 19
- The Dallas Stars defeat the Buffalo Sabres in triple overtime of game six of the Stanley Cup Finals to win their first Stanley Cup. Brett Hull scores the controversial cup-winning goal to seal the victory. [20]
- June 25
- The San Antonio Spurs defeat the New York Knicks 78-77 in Game 5 of the NBA Finals to take home the title in a strike-shortened season. [20]
- June 30
- After a loss at Wimbledon, Boris Becker announces that he will end his tennis career. [37]
- July 7
- In Rome, Hicham El Guerrouj runs the fastest mile ever recorded - 3:43:13. [20]
- July 18
- David Cone pitches a perfect game, the 16th in history, as the New York Yankees defeat the Montreal Expos, 6-0, to celebrate Yogi Berra Day. [20]
- July 25
- Lance Armstrong wins his first Tour de France (cycling). [20]
- August 13
- Steffi Graf announces her retirement from tennis after a 17 year career in which she won 107 career titles including 22 Grand Slams. [20]
- August 17
- Baltimore Orioles' pitcher Jesse Orosco sets a major league mark pitching in his 1,072nd game. [56]
- August 26
- Michael Johnson captures the 400m world record. [20]
- September 11
- Death of Gonzalo Rodriguez, Uruguyan race car driver (born 1972). [20]
- Eric Milton of the Minnesota Twins pitches a 7-0 no-hitter against the Anaheim Angels. [20]
- October 6
- Death of Gorilla Monsoon, American professional wrestler and announcer (born 1937). [20]
- October 8
- Death of John McLendon, American basketball coach (born 1915). [20]
- October 12
- Death of Wilt Chamberlain, American basketball player (born 1936). [5] [20]
- October 25
- Death of Payne Stewart, American golfer (plane crash) (born 1957). [20]
- October 27
- The New York Yankees complete a four-game sweep of the Atlanta Braves to win their second consecutive World Series of basevall. [20] [56]
- October 31
- Death of Greg Moore, Canadian race car driver (born 1975). [20]
- November 1
- Death of Walter Payton, American football player (born 1954). [20]
- November 22
- Wayne Gretzky is inducted into the Hockey Hall of Fame, his number 99 permanently retired by the National Hockey League. [20]
- November 28
- The Hamilton Tiger-Cats defeat the Calgary Stampeders 32-21 to win the 87th Grey Cup at B.C. Place Stadium in Vancouver. [20]
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