1985
- April
- In Canada, British Columbia starts its own lottery company. [40.20]
- (month unknown)
- Maine, New Hampshire, and Vermont state governments form the TriState Lottery, offering the Tri-State Megabucks lotto. [187.390]
- July
- Montana legalizes video poker machines in licensed liquor establishments. [87.51]
- August 23
- Paul Hornung awarded US$1,160,000 by a Louisville court against NCAA who barred him as a college football analyst for betting on games. [1]
- September 12
- In Canada, the Lotto 6/49 lottery expands to two weekly draws, with the first Wednesday evening draw. [40.138]
- Year
- Lottery ticket sales in Canada: CDN$2.7 billion. [40.9]
1986
- January 18
- New York Lotto pays US$30.5 million to one winner (numbers are 19-20-27-34-41-46). [1]
- March 2
- First million-dollar purse for a handicap race won at Santa Anita. [1]
- March 6
- International Game Technology introduces the Megabucks progressive slot machine network in nine casinos in Las Vegas, Nevada. The system pools bets across the network, allowing huge jackpots. [87.51] [187.480]
- March
- In Montreal, Canada, one person wins CDN$7.6 million on the Lotto 6/49 draw. [40.101]
- June
- At the Harrah's Tahoe casino, the largest slot machine jackpot is won, US$3 million. [87.20]
- July 5
- The newly recognized sovereign tribe Mashantucket Pequot open a US$4 million bingo hall on tribal land in Connecticut, USA. Construction was funded by a loan from the United Arab-American Bank. (By 2004 it becomes the world's most profitable casino.) [187.xvii,437]
- November
- The Las Vegas Hilton Matchplay Blackjack Championship II is held. [312.22]
1987
- February 1
- Terry Williams of Los Gatos, California wins US$5 million at Harrah's Reno playing the MegaBuck slot machine, after spending US$47. [87.19]
- February
- The US Supreme Court rules on California v. Cabazon Band of Mission Indians: If a state legalized a form of gambling, tribes could also offer it, with no outside interference. [187.435]
- (month unknown)
- The US Supreme Court rules in the landmark case, California v. Cabazon Band of Mission Indians. The Court upholds the right under federal law for Indians to run gambling operations without state regulation in states where such gaming is legal for any purpose. [39]
- French government legalizes slot machines. [187.468]
- December 24
- In the USA, the Illinois State Lottery draw for US$39.5 million is split between four winners. [40.28]
1988
- February 14
- At the Cal Neva Club casino in Reno, Nevada, Cammie Brewer wins the largest slot machine jackpot of US$6.8 million on a Megabucks machine, after playing about US$20. [87.20]
- (month unknown)
- Florida state legalizes a state lottery. [187.388]
- A Florida woman wins a lottery draw of US$55.1 million. [40.40]
- August 9
- Just one day after 8/8/88 New York lottery's daily number is 888. [1]
- October 30
- Two gambling clubs and one player share US$61.38 million California lotto jackpot. [1]
- December 3
- New York Lotto pays US$45 million to twelve winners (numbers are 1-8-13-18-28-48). [1]
- December 24
- In Spain, the El Gordo lottery draw first prize is US$194 million, shared by 72 winners. [40.41]
- December 28
- A couple in Montreal, Quebec, Canada, holds 28 tickets for the Lotto 6/49 lottery draw that day. Every one wins, with between 3 and 5 winning numbers per ticket. Total win is CDN$5260. [40.43]
1989
- February 22
- New York Lotto pays US$26.9 million to one winner (numbers are 1-5-12-19-44-50). [1]
- April 1
- In Canada, four people share a Canadian record CDN$15.5 million Lotto 6/49 jackpot. [40.82]
- April 12
- In Canada, four people share a CDN$14.2 million Lotto 6/49 jackpot. [40.82]
- April 15
- Largest lottery win to date in North America (US$69 million) drawn in Illinois. [1]
- (month unknown)
- South Dakota legalizes limited-stakes casino gambling in the mining town of Deadwood. [39]
- Iowa and Illinois legalize riverboat casino gaming. [39]
- August
- Iowa legislature passes a riverboat gaming act, legalizing gambling in licensed boats on several rivers, if approved by the adjacent county. [187.440]
- August 24
- Record-setting baseball player Pete Rose agrees to a lifetime ban from the sport following allegations of illegal gambling, thereby preventing his induction into the Baseball Hall of Fame. [1] [43]
- October 28
- In Canada, four people share a CDN$14 million Lotto 6/49 jackpot. [40.82]
- November 1
- South Dakota begins legal gambling in Deadwood city. [187.443]
- November 22
- The Mirage hotel and casino opens in Las Vegas, Nevada. On the opening night, Elmer Sherwin wins US$4.6 million on a Megabucks spin. About 200,000 people attend the opening. [187.298a,482]
- December
- In Winnipeg, Manitoba, Canada, the provincial government opens the Crystal Casino, the first permanent casino in the country, in the Fort Gary Hotel. [40.21,122]
- Year
- Soviet Union citizens spent US$700 million on draw, loto, and instant-win tickets. [187.474]
1990
- January 6
- New York Lotto pays US$35 million to one winner (numbers are 18-25-26-32-42-44). [1]
- January
- Illinois state passes a riverboat gambling act. [187.441]
- April 11
- New York Lotto pays US$35 million to two winners (numbers are 6-14-24-32-34-51). [1]
- (month unknown)
- Colorado voters approve limited-stakes casino gambling in three former mining towns: Cripple Creek, Black Hawk, and Central City. [39]
- West Virginia is the first US state to authorize slot machines and video lottery terminals at racetracks. [187.376]
- September 15
- Florida lottery goes over US$100,000,000. [1]
- September 22
- In Canada, three people share a CDN$15 million Lotto 6/49 jackpot. [40.82]
- October 27
- In Canada, 18 people share a Canadian record CDN$19.8 million Lotto 6/49 jackpot. [40.82]
- Year
- Lottery ticket sales in the USA: US$20 billion, net profit US$10 billion. [40.13]
1991
- January 26
- New York Lotto pays US$90 million to nine winner (numbers are 5-15-30-35-46-50). [1]
- March 9
- In Canada, one person wins a CDN$13.2 million Lotto 6/49 jackpot. [40.82]
- March 16
- New York Lotto pays US$33.3 million to one winner (numbers are 18-21-32-33-35-38). [1]
- April 1
- In Iowa, USA, riverboat gambling is legalized, as the Diamond Lady is launched. [187.441]
- April
- Iowa launches the first gaming vessel in recent U.S. history. [39]
- June 29
- In Canada, one person wins a Canadian record (for a single winner) CDN$13.9 million Lotto 6/49 jackpot. [40.82]
- October 26
- In Canada, two people share a CDN$15 million Lotto 6/49 jackpot. [40.82]
- December
- The 14th World Championship of Blackjack is held at the Aladdin Hotel and Casino in Las Vegas. Over 650 players take part. Rod Boone wins US$100,000 grand prize. [312.22]
- December 21
- 95 share in Madrid, Spain $1.3 billion lottery (number47996). [1]
1992
- February 15
- The Mashantucket Pequot Tribal Nation opens the Foxwoods Resort Casino in Ledyard, Connecticut, with financing from Malaysian billionaire Lim Goh Tong. [187.437] [208.40]
- February
- In the USA, the Florida state lottery draw gives an unshared win of US$15.5 million to a resident of Ontario, Canada. Winning numbers are 2, 6, 23, 33, 40, 48. [40.40]
- The 3rd Annual Knights of Blackjack Tournament is held at the Stardust Resort and Casino in Las Vegas. 587 players take part. Ed Del Toro wins US$100,000. [312.22]
- May 30
- New York Lotto pays US$30 million to one winner (numbers are 12-15-30-33-40-48). [1]
- (month unknown)
- Louisiana becomes the third US state to legalize land-based casino gambling. [39]
- Multistate Lottery Corporation ends Lotto America, and starts Powerball, in which players pick 5 numbers from 45, and 1 number from 45. [187.390]
- Sun International opens the Lost City casino resort complex at Sun City, Bophuthatswana in South Africa. [187.466]
- Nineteen University of Maine football and baseball players are suspended for participating in a US$10,000 per week gambling operation. [328.38]
- September 26
- In Canada, three people share a CDN$18 million Lotto 6/49 jackpot. [40.82]
1993
- April 3
- In Canada, two people share a CDN$15 million Lotto 6/49 jackpot. [40.82]
- (month unknown)
- In Las Vegas, Nevada, USA, Circus Circus' pyramidal Luxor opens, featuring an Egyptian theme and amusement park. [39]
- The Casino de Montréal opens in Québec, Canada. [187.462]
- In the USA, the Wisconsin Powerball lottery grand prize of US$111 million is won by a couple. [40.40]
- August 1
- Riverboat gambling is launched in Mississippi state. [187.442]
- September
- In Canada, the last draw of the Provincial lottery is held. [40.154]
- October 23
- In Canada, one person wins a Canadian record (for a single winner) CDN$15 million Lotto 6/49 jackpot. [40.82]
- Year
- 92 million people visit casinos in the USA. [39]
1994
- January 1
- In Canada, a Celebration '94 ticket on the Lotto 6/49 lottery gives CDN$1 million to a Toronto resident. [40.35]
- March
- Six people in Quebec, Canada, share a CDN$19 million Lotto 6/49 lottery jackpot, the largest single ticket in Canadian history. [40.63]
- April
- The April Shower of Money blackjack tournament is held at the Stardust Resort and Casino in Las Vegas. John Ressman wins US$100,000. [312.22]
- (month unknown)
- Voters in Iowa vote to eliminate wager and loss limits in riverboat casinos. [39]
- In Ontario, Canada, Casino Windsor opens. [187.462]
- Great Britain introduces the National Lottery, run by the Camelot company. Participants choose 6 of 49 numbers in a weekly draw. [187.473]
- November 19
- First National Lottery draw in England. [1]
- December
- The National Blackjack Finals tournament is held at the Riviera Casino in Las Vegas. 612 players coompete. Clinton Borland wins US$100,000. [312.23]
1995
-
- In Nova Scotia, Canada, government-owned casinos first open. [187.462]
- November 11
- In New Orleans, Louisiana, USA, the casino venture files for Chapter 11 bankruptcy. [39]
- December 16
- Death of Johnny Moss, American poker player (born 1907). [29]
- Year
- Legal gambling in the United States grosses over US$40 billion in revenues. [39]
- Worldwide sales for legal lotteries: US$95 billion. #1 is USA at US$28.7 million, #2 is Germany at US$9.2 billion. [39]
1996
- January 1
- California begins a three-year moratorium on new cardclubs in the state. [39]
- January 6
- Record US$65.2 million British lottery won by three people (2-3-4-13-42-44). [1]
- June 24
- California Supreme Court rules in the case of Western Telcon v. California State Lottery. The court rules that the lottery's electronic keno game is not a lawful lottery game, but an illegal banked game. [39]
- (month unknown)
- The Casino di Liban re-opens in Beirut, Lebanon. [187.459]
- South Africa passes the National Gaming Act, authorizing a national lottery and up to 40 casinos. [187.467]
- Thirteen Boston College football players are suspended after betting on college and professional games. [328.38]
- August
- First legal tournament-play site on the Internet opens: Blackjack Time on CasinoTime.com. [312.23]
- November
- In Louisiana, USA, casino gaming is ratified in a referendum. [39]
- Year
- Sports wagering online: US$60 million. [328.99]
1997
-
- World Sports Exchange of Antigua goes online as the first full-service Internet sports book, with online betting. [187.489]
- July 2
- Tom Walters Sr. of Meridian, Mississippi wins powerball of US$11 million. [18]
1998
- March 4
- US Attorney General Janet Reno declares it is illegal to transmit sports-wagering info over telephone lines, including the Internet. [328.105]
- March 6
- Matt Beck, an angry lottery accountant kills four at Connecticut state lottery. [1]
- (month unknown)
- The Oasis Casino opens in Jericho under the Palestinian Authority. [187.458]
- November 22
- Death of Stu Unger, professional poker player (born 1953). [19]
- Year
- Sports wagering online: US$600 million. [328.99]
1999
-
- The National Gambling Impact Study Commission find no significant presence of organized crime in legal US gambling. [187.418]
- The North Korean government opens the Emperor Casino in Raijin, open to foreigners only. [187.457]
- Belgium's parliament declares casinos legal, and allows slot machines. [187.470]
- Circus Circus Enterprises opens the Mandalay Bay casino in Las Vegas. [187.484]
- The Lasseters casino of Alice Springs, Northern Territory, Australia, is the first land-based casino to go online on the Internet. [187.491]
- November
- The US Senate passes the Internet Gambling Prohibition Act, which makes operating a virtual casino or sports book on the Internet a federal crime. [328.100]
- Year
- Sports wagering online: US$1.2 billion. [328.99]
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