• Alpine Skiing World Cup
  • Men's overall season champion: Lasse Kjus, Norway
  • Women's overall season champion: Alexandra Meissnitzer, Austria

• Super Bowl XXXIII – the Denver Broncos (AFC) won 34–19 over the Atlanta Falcons (NFC)
  • Location: Pro Player Stadium
  • Attendance: 74,803
  • MVP: John Elway, QB (Denver)
• April 17 – Quarterback Tim Couch is selected by the Cleveland Browns with the first overall pick in the 1999 NFL Draft.
• St. Louis Rams Quarterback Kurt Warner named NFL MVP
• St. Louis Rams Head coach Dick Vermeil named NFL Coach of the Year
• Indianapolis Colts running back Edgerrin James named NFL Rookie of the Year
• Fiesta Bowl (1998 season):
  • The Tennessee Volunteers claim the first ever BCS National Championship 23–16 over the Florida State Seminoles
• November 1 – death of Walter Payton (45), Chicago Bears running back

• 1999 World Artistic Gymnastics Championships – held in Tianjin, China
  • Women's team champions: Romania
  • Women's all-around champion: Maria Olaru, Romania
  • Women's vault champion: Elena Zamolodchikova, Russian Federation
  • Women's floor exercise champion: Andreea Răducan, Romania
  • Women's uneven bars champion: Svetlana Khorkina, Russian Federation
  • Women's balance beam champion: Ling Jie, China
  • Men's team champions: China
  • Men's all-around champion: Nikolai Kryukov, Russian Federation
  • Men's horizontal bar champion: Jesús Carballo, Spain
  • Men's parallel bars champion: Lee Joo-hyung, South Korea
  • Men's pommel horse champion: Alexei Nemov, Russian Federation
  • Men's floor exercise champion: Alexei Nemov, Russian Federation
  • Men's still rings champion: Dong Zhen, China
  • Men's vault champion: Li Xiaopeng, China

• Champions League – Manchester United F.C. beat FC Bayern Munich 2 – 1 to win the treble having already won the English premiership and FA Cup.^[1]
• UEFA Cup – Parma F.C. beat Olympique Marseille 3–0
• Copa Libertadores – Palmeiras beat Deportivo Cali 4–3 after penalties
• Asian Club Championship – Júbilo Iwata beat Esteghlal 2-1
• CAF Champions League – Raja Casablanca beat Espérance 4-3 after penalties
• FIFA Women's World Cup – USA beat China 5-4 after penalties.^[2]

• August – 1999 World Championships in Athletics held at Seville
• Hicham El Guerrouj sets a new world record for the mile.^[3] He recorded a time of 3:43.13, barely edging out Noah Ngeny who recorded 3:43.40.
• Michael Johnson sets a new world record in the 400 metres in 43.18.^[4]

• May 10 – The Boston Red Sox beat the Seattle Mariners, 12–4, as shortstop Nomar Garciaparra hits three home runs, including two grand slams; one in the first inning, and one in the eighth. Nomar is the 9th in MLB history (the first since Robin Ventura in 1995) to hit two grand slams in the same game, and the first Red Sox player to accomplish the feat since Jim Tabor in 1939.
• July 18 – David Cone pitches a perfect game, the 16th in history, as the Yankees defeat the Montreal Expos, 6–0, to celebrate Yogi Berra Day.
• Texas Rangers Catcher Iván Rodríguez named AL MVP
• Atlanta Braves 3B Chipper Jones named NL MVP
• Kansas City Royals OF Carlos Beltrán named AL Rookie of the Year
• Cincinnati Reds Pitcher Scott Williamson named NL Rookie of the Year
• World Series – New York Yankees won 4 games to 0 over the Atlanta Braves. The series MVP: Mariano Rivera, New York
• Miami Hurricanes defeat Florida State Seminoles in the College World Series

• 1999 NBA Finals – the San Antonio Spurs defeat the New York Knicks, 4 games to 1, to win the franchise's first championship. The Spurs also became the first former ABA team to win an NBA title, while the Knicks were the first number eight seed in NBA history to make it to the NBA Finals. This season also marked the beginning of both the Spurs dynasty and the Tim Duncan era, who would win 4 more championships in the next 15 years.
• Utah Jazz forward Karl Malone named NBA MVP for the second time in his career
• Toronto Raptors Guard/Forward Vince Carter named NBA Rookie of the Year
• NCAA Men's Basketball Championship –
  • Connecticut wins 77–74 over Duke
• Duke Blue Devils forward Elton Brand named Naismith College Player of the Year & John R. Wooden Award
• WNBA Finals – The Houston Comets defeat the New York Liberty, 2 games to 1, to win their third title in a row.
• National Basketball League (Australia) Finals:
  • Adelaide 36ers defeated the Victoria Titans 2–1 in the best–of–three final series.

• July 31 to August 8 – Pan American Games held at Winnipeg
• August 20 to August 27 – 1999 World Amateur Boxing Championships held at Houston
• September 18 – The Fight of the Millennium:
  • Félix Trinidad defeats Oscar De La Hoya by split 12-round decision to unify the IBF and WBC's world Welterweight championships.

• Grey Cup – Hamilton Tiger-Cats win 32–21 over the Calgary Stampeders
• Vanier Cup – Laval Rouge et Or win 14–10 over the Saint Mary's Huskies

• Cricket World Cup Final: Australia beat Pakistan by eight wickets
• Playing for Himachal Pradesh against Jammu and Kashmir in the Ranji Trophy, Rajiv Nayyar becomes the first and only player in first-class cricket history to bat for over 1,000 minutes in an innings, scoring 271 in 1,015 minutes.^[5]

• World Curling Championships –
  • Men: Scotland won 6–5 over Canada
  • Women: Sweden won 8–5 over USA

• Giro d'Italia won by Ivan Gotti of Italy
• Tour de France – Lance Armstrong of the United States
• UCI Road World Championships – Men's road race – Óscar Freire of Spain

• Iditarod Trail Sled Dog Race Champion –
  • Doug Swingley with lead dogs: Stormy, Cola & Elmer

• Men's Champions Trophy: Australia
• Women's Champions Trophy: Australia

• World Figure Skating Championship –
  • Men's champion: Alexei Yagudin, Russia
  • Ladies' champion: Maria Butyrskaya, Russia
  • Pairs' champions: Yelena Berezhnaya & Anton Sikharulidze, Russia
  • Ice dancing champions: Anjelika Krylova & Oleg Ovsyannikov, Russia
• European Figure Skating Championships –
  • Men's champion: Alexei Yagudin, Russia
  • Ladies' champion: Maria Butyrskaya, Russia
  • Pairs' champions: Maria Petrova & Alexei Tikhonov, Russia
  • Ice dancing champions: Anjelika Krylova & Oleg Ovsyannikov, Russia

• Women's World Floorball Championships
  • Champion: Finland
• European Cup
  • Men's champion: Warberg IC
  • Women's champion: Tapanilan Erä

• Camogie
  • All–Ireland Camogie Champion: Tipperary
  • National Camogie League: Cork
• Gaelic football
  • All-Ireland Senior Football Championship – Meath 1–11 beat Cork 1–8
  • National Football League – Cork 0–12 beat Dublin 1–7
• Ladies' Gaelic football
  • All–Ireland Senior Football Champion: Mayo
  • National Football League: Monaghan
• Hurling
  • All-Ireland Senior Hurling Championship – Cork 0–13 beat Kilkenny 0–12
  • National Hurling League – Tipperary 1-14 beat Galway 1-10

• October 25 – death of Payne Stewart (42) in an air accident

Men's professional

• Masters Tournament – José María Olazábal
• U.S. Open – Payne Stewart
• British Open – Paul Lawrie This Open is also remembered for the epic collapse of French golfer Jean van de Velde, who threw away a three–shot lead on the final hole, finding himself in a playoff which Lawrie won.
• PGA Championship – Tiger Woods
• PGA Tour money leader – Tiger Woods – $6,616,585
• PGA Tour Player of the Year – Tiger Woods
• PGA Tour Rookie of the Year – Carlos Franco
• Senior PGA Tour money leader – Bruce Fleisher – $2,515,705
• Ryder Cup – United States won 14½ to 13½ over Europe in team golf.

Men's amateur

• British Amateur – Graeme Storm
• U.S. Amateur – David Gossett
• European Amateur – Grégory Havret

Women's professional

• Nabisco Dinah Shore – Dottie Pepper
• LPGA Championship – Juli Inkster
• U.S. Women's Open – Juli Inkster
• Classique du Maurier – Karrie Webb
• LPGA Tour money leader – Karrie Webb – $1,591,959

• 1999 World Men's Handball Championship – won by Sweden
• 1999 World Women's Handball Championship – won by Norway

• North America Cup – The Panderosa
• United States Pacing Triple Crown races –
  1. Cane Pace – Blissful Hall
  2. Little Brown Jug – Blissful Hall
  3. Messenger Stakes – Blissful Hall
• United States Trotting Triple Crown races –
  1. Hambletonian – Self Possessed
  2. Yonkers Trot – CR Renegade
  3. Kentucky Futurity – Self Possessed
• Australian Inter Dominion Harness Racing Championship –
  • Pacers: Sir Vancelot
  • Trotters: Special Force

Steeplechases

• Cheltenham Gold Cup – See More Business
• Grand National – Bobbyjo

Flat races

• Australia – Melbourne Cup won by Rogan Josh
• Canada – Queen's Plate won by Woodcarver
• Dubai – Dubai World Cup won by Almutawakel
• France – Prix de l'Arc de Triomphe won by Montjeu
• Ireland – Irish Derby Stakes won by Montjeu
• Japan – Japan Cup won by Special Week
• English Triple Crown races:
  1. 2000 Guineas Stakes – Island Sands
  2. The Derby – Oath^[6]
  3. St Leger Stakes – Mutafaweq
• United States Triple Crown races:
  1. Kentucky Derby – Charismatic
  2. Preakness Stakes – Charismatic
  3. Belmont Stakes – Lemon Drop Kid
• Breeders' Cup World Thoroughbred Championships:
  1. Breeders' Cup Classic – Cat Thief
  2. Breeders' Cup Distaff – Beautiful Pleasure
  3. Breeders' Cup Filly & Mare Turf – Soaring Softly (inaugural running of this race)
  4. Breeders' Cup Juvenile – Anees
  5. Breeders' Cup Juvenile Fillies – Cash Run
  6. Breeders' Cup Mile – Silic
  7. Breeders' Cup Sprint – Artax
  8. Breeders' Cup Turf – Daylami

• February 13: Last ice hockey game played at the historic Maple Leaf Gardens in Toronto, the game was a 6–2 loss for the Toronto Maple Leafs to Chicago Blackhawks.
• Wayne Gretzky played his last NHL game on April 18, 1999, at Madison Square Garden where the New York Rangers lost 2–1 in overtime to the Pittsburgh Penguins
• Art Ross Trophy as the NHL's leading scorer during the regular season: Jaromir Jagr, Pittsburgh Penguins
• Hart Memorial Trophy for the NHL's Most Valuable Player:
  • Jaromir Jagr – Pittsburgh Penguins
• Stanley Cup – Dallas Stars defeat the Buffalo Sabres 4 games to 2, Conn Smythe Trophy – Joe Nieuwendyk. The Stars became the first team from the Southern United States to win the Cup.
• World Hockey Championship
  • Men's champion:Czech Republic defeated Finland
  • Junior Men's champion: Russia defeated Canada
  • Women's champion: Canada defeated the United States
• NCAA men's ice hockey championship – University of Maine Black Bears defeat University of New Hampshire Wildcats 3–2 in overtime

• Major League Lacrosse (MLL) is founded by Jake Steinfeld, Dave Morrow and Tim Robertson.
• The Toronto Rock beat the Rochester Knighthawks 13–10 to win the National Lacrosse League Championship.
• The Victoria Shamrocks win the Mann Cup.
• The Edmonton Miners win the Founders Cup.
• The Whitby Warriors win the Minto Cup.

The following is a list of major noteworthy MMA events during 1999 in chronological order.

• First IARU Region II Amateur Radio Direction Finding Championships held in Portland, Oregon, United States This is the first IARU sanctioned international ARDF competition in the Americas.
• Third High Speed Telegraphy World Championship held in Pordenone, Italy.

• April 23 at Sydney, Australia – 1999 ANZAC test match is won by Australia 20–14 against New Zealand at Stadium Australia before 30,245.
• June 23 at Brisbane, Australia – 1999 State of Origin is retained by Queensland as the third and deciding match of the series is drawn 10 – 10 with New South Wales.
• September 19 in Australia – last game of the 1999 Telstra Premiership is played, including the final NRL matches as stand alone entities for the Balmain Tigers and Western Suburbs Magpies who would later merge to form the Wests Tigers.
• September 26 at Sydney, Australia – 1999 NRL season culminates in the Melbourne Storm's 20 – 18 win against the St George Illawarra Dragons in the grand final
• October 9 at Manchester, England – Super League IV culminates in St. Helens' 8 – 6 win against the Bradford Bulls in the grand final.
• November 1 at Auckland, New Zealand – 1999 Tri–Nations culminates in Australia's 22 – 20 win against New Zealand in the final.

• 105th Five Nations Championship series, the last under the Five Nations format, is won by Scotland. The modern Six Nations format would be established the following year with the addition of Italy.
• Bledisloe Cup – Australia retains the cup after drawing the two-match series with New Zealand.
• Rugby World Cup: Australia defeat France 35–12 in the final, becoming the first nation to win the Webb Ellis Cup twice.
• Tri Nations – New Zealand

• World Snooker Championship – Stephen Hendry beats Mark Williams 18–11
• World rankings – John Higgins remains world number one for 1999/2000

• Fourth World Short Course Championships, held in Hong Kong, China (April 1 – 4)
  • Australia wins the most medals (27), and the most gold medals (9)
• 24th European LC Championships, held in Istanbul, Turkey (July 26 – August 1)
  • Germany wins the most medals (23), and the most gold medals (11)
• XIII Pan American Games, held in Winnipeg, Manitoba, Canada (August 2–7)
• Eighth Pan Pacific Championships, held in Sydney, Australia (August 22–29)
• Third European SC Championships, held in Lisboa, Portugal (December 9–12)
  • Germany wins the most medals (26), Sweden the most gold medals (9)
• February 17 – Australia's Susie O'Neill snapped the oldest world record in the books, clocking 2:05.37 in the women's 200m butterfly (short course) at a World Cup meet in Malmö, Sweden. The old mark, set by Mary T. Meagher on January 2, 1981, stood at 2:05.65.
• September 2 – Susie O'Neill breaks her own world record in the women's 200m butterfly (short course) at a meet in Canberra, Australia, clocking 2:04.43

• World Championships held in Edmonton, Alberta, Canada

• Grand Slam in tennis men's results:
  1. Australian Open – Yevgeny Kafelnikov
  2. French Open – Andre Agassi
  3. Wimbledon championships – Pete Sampras
  4. U.S. Open – Andre Agassi
• Grand Slam in tennis women's results:
  1. Australian Open – Martina Hingis
  2. French Open – Steffi Graf
  3. Wimbledon championships – Lindsay Davenport
  4. U.S. Open – Serena Williams
• Davis Cup – Australia won 3–2 over France in world tennis.
• Kim Clijsters makes her WTA Tour debut.

• Men's World League: Italy
• Women's World Grand Prix: Russia
• Men's European Championship: Italy
• Women's European Championship: Russia

• Men's European Championship: Hungary
• Men's World Cup: Hungary
• Women's European Championship: Italy
• Women's World Cup: Netherlands

• 13th Pan American Games held in Winnipeg, Manitoba, Canada^[7]
• Seventh All–Africa Games held in Johannesburg, South Africa
• Winter Asian Games held in Gangwon, South Korea
• Ninth Pan Arab Games held in Amman, Jordan
• 20th Southeast Asian Games held in Bandar Seri Begawan, Brunei Darussalam
• 20th Summer Universiade held on Palma de Mallorca, Spain
• 19th Winter Universiade held in Poprad, Slovakia

• Associated Press Male Athlete of the Year – Tiger Woods, PGA golf
• Associated Press Female Athlete of the Year – United States women's national soccer team, soccer