April 9, 1989 - Accused of striking a parking attendant three times with an open hand outside a Los Angeles nightclub after the attendant asked Tyson to move his Mercedes-Benz out of a spot reserved for the club's owner. The charges are later dropped due to lack of witness cooperation.
July 21, 1989 - Tyson knocks out Carl "The Truth" Williams to retain the world heavyweight title.
Feb. 11, 1990 - In a stunning upset, Tyson is knocked out by James "Buster" Douglas in the 10th round and loses his world heavyweight title.
Nov. 1, 1990 - A New York City civil jury awards Sandra Miller $100 for battery after an incident in which boxer Tyson grabbed her breasts, insulted and propositioned her. The jury found Tyson's behavior "not outrageous."
June 28, 1991 - In his last fight before his legal problems, Tyson defeats Razor Ruddock in 12 rounds.
July 18, 1991 - Tyson meets Desiree Washington, a Miss Black America contestant, at a pageant rehearsal. They go to the boxer's hotel room in the early morning hours.
July 22, 1991 - Washington files a complaint with police accusing Tyson of rape.
Sept. 9, 1991 - A special grand jury indicts Tyson on rape and three other charges. Two days later, he is booked in Indianapolis and released on $30,000 cash bond.
Feb. 10, 1992 - After nine hours of deliberation, Tyson is found guilty on one count of rape and two counts of deviate sexual conduct.
March 26, 1992 - Superior Court Judge Patricia Gifford sentences Tyson to 10 years in prison, suspending four. She orders him to serve the term immediately.
May 8, 1992 - Tyson is found guilty of threatening a guard and disorderly conduct in prison, adding 15 days to his sentence.
Oct. 28, 1992 - Tyson's father, Jimmy Kirkpatrick, dies in Brooklyn, N.Y. Tyson does not ask for a leave to attend the funeral.
Aug. 6, 1993 - By a 2-1 vote, the Indiana Court of Appeals upholds Tyson's conviction.
Sept. 2, 1993 - The Indiana Supreme Court denies Tyson's appeal without comment.
March 25, 1995 - Tyson is released from the Indiana Youth Center near Plainfield, Indiana.
Aug. 19, 1995 - Begins comeback with 89 seconds victory over Peter McNeeley in Las Vegas.
Dec. 16, 1995 - Knocks out Buster Mathis, Jr. in third round in Philadelphia.
March 16, 1996 - Knocks out Frank Bruno in third round to win the WBC heavyweight title in Las Vegas.
Sept. 7, 1996 - Knocks out Bruce Seldon in first to win the WBA heavyweight title in Las Vegas. Stripped by WBC immediately after fight for not fighting mandatory challenger Lennox Lewis.
Nov. 9, 1996 - Loses to Evander Holyfield when referee Mitch Halpern stops the bout in the 11th round.
June 28, 1997 - Tyson is disqualified after the third round of his rematch with Holyfield after he bites Holyfield twice, once on each ear. Tyson claims he was retaliating for a head butt inflicted by Holyfield that opened up a gash above his right eye. Referee Mills Lane ruled the butt was accidental.
July 9, 1997 - The Nevada State Athletic Commission, in a unanimous voice vote, revoked Tyson's boxing license and fined him $3 million for biting Holyfield.
Oct. 16, 1997 - Ordered to pay boxer Mitch Green $45,000 even though a jury ruled the former heavyweight champion was provoked into a Harlem street fight in 1988.
Oct. 29, 1997 - Broke a rib and punctured a lung on his right side when his motorcycle skidded off a Connecticut highway after hitting a patch of sand.
March 5, 1998 - Filed a $100 million lawsuit in U.S. District Court in New York against Don King, accusing the promoter of cheating him out of tens of millions of dollars.
March 9, 1998 - Filed a lawsuit against former managers Rory Holloway and John Horne, claiming they betrayed him by arranging a deal that made King the former heavyweight champion's exclusive promoter.
March 9, 1998 - Sherry Cole and Chevelle Butts filed a $22 million lawsuit against Tyson claiming he verbally and physically abused them March 1 at a Washington bistro after his sexual advances toward one of them were spurned.
July 16, 1998 - The 2nd U.S. Circuit Court of Appeals reinstated a $4.4 million award that a jury decided boxer Tyson owes former trainer Kevin Rooney for unjustly firing him.
July 17, 1998 - Applied for a boxing license in New Jersey.
July 29, 1998 - Appeared before the New Jersey Athletic Control Board to get a boxing license to resume his career. Tyson first choked back tears as he apologized for biting Evander Holyfield's ears. At the end of his 35-minute appearance, however, Tyson cursed in front of regulators after being continually questioned about biting Holyfield.
Aug. 13, 1998 - On the eve of a meeting of the New Jersey Athletic Control Board, Tyson's advisers abruptly withdrew his application for a New Jersey boxing license.