September 9, 1991 - Indianapolis, Indiana grand jury indicts Tyson on one count of rape, two counts of criminal deviant behavior and one count of confinement. The charges stem from the rape claims of Desiree Washington, a contestant in the Miss Black America Pageant in July of 1991.
February 10, 1992 - Tyson is convicted of one count of rape and two counts of deviate sexual conduct involving Miss Black America Pageant contestant Desiree Washington in 1991.
March 26, 1992 - Judge sentences Tyson to 10 years on each of count rape and two criminal counts of deviant conduct, to be served concurrently. Tyson also incurs a $30,000 fine and revocation of bail. After sentencing he is sent to a medium security prison, the Indiana Youth Center in Plainfield, Indiana.
August 6, 1992 - The rape conviction is upheld by Indiana Court of Appeals.
March 7, 1994 - The U.S. Supreme Court refuses to hear Tyson rape case appeal.
March 25, 1995 - Is released early from the Indiana Youth Center after serving three years and six weeks. Conditions of the release include four years probation with 100 hours of community service per year and psychological counseling.
August 19, 1995 - Returns to the ring and needs only seven seconds to knock Peter McNeeley to the canvas. After a second knockdown the match is stopped at 89 seconds, and Tyson declared the winner on a TKO.
March 16, 1996 - Regains WBC championship from Frank Bruno in a third round TKO.
November 9, 1996 - Loses to Evander Holyfield TKO in the eleventh round.
June 28, 1997 - Tyson loses the Holyfield rematch, after being disqualified in the third round for biting Holyfield's ears. He is also fined $3 million, 10% of his purse, and his Nevada boxing license is revoked for one year. The Nevada revocation is voluntarily honored nationwide.
March 5, 1998 - Files a $100 million lawsuit against Don King, accusing the promoter of fraud and cheating him out of tens of millions of dollars.
October 19, 1998 - Nevada boxing license reinstated, more than 15 months after it was revoked.
December 1, 1998 - Tyson pleads no contest to two counts of misdemeanor assault of two motorists after a traffic accident in Gaithersburg, Maryland, August 31, 1998.
February 5, 1999 - Tyson is sentenced to serve one year in jail for assaulting two motorists after a traffic accident in 1998. The official sentence is two years for each assault, with all but one year suspended, 200 hours of community service, a fine of $2,500 for each count of assault, two years' probation following completion of the jail term and continued therapy.
May 24, 1999 - Early release from the Montgomery County Jail, in Rockville, Maryland. Tyson is freed after serving three and a half months of a 14-month sentence when Maryland and Indiana agree to grant his release.
January 22, 2002 - Throws a punch at a Lennox Lewis bodyguard at a news conference announcing Tyson's scheduled challenge to Lewis on April 6 in Las Vegas.
January 29, 2002 - Nevada denies boxing license for April 6 bout with Lennox Lewis after altercation at New York press conference between Lewis and Tyson. Fight rescheduled for June 8 in Memphis.
June 8, 2002 - Knocked out by Lennox Lewis in the eighth round. It is the last title fight of Tyson's career.
June 21, 2003 - Arrested outside Brooklyn Marriott Hotel after a brawl with two fans.
August 1, 2003 - Files for bankruptcy, records showing $38 million in debt, $13.4 million of it owed to the IRS and $4 million owed for British taxes.
February 26, 2004 - Pleads guilty to disorderly conduct in connection to the June 2003 incident and agrees to perform 100 hours of community service and to undergo six months of psychiatric counseling.
July 30, 2004 - Loses to Danny Williams by a knock out in the fourth round.
2005 - Settles lawsuit with Don King for $14 million
June 11, 2005 - Loses to Kevin McBride in the sixth round by a TKO
June 12, 2005 - Announces retirement.