Events concerning the Grand Theft Auto series in 1999.
Real World Events
- Grand Theft Auto: London 1969 and Grand Theft Auto: London 1961 are released (latter is a free download).
- Grand Theft Auto 2 is released on the PlayStation in North America on October 22.
- GTA 2 is released on the PC on October 27.
- Mock police records on the Grand Theft Auto 2 website are dated between 13/07/13 and 03/11/13 . This, along with the game's futuristic setting led some fans to believe that the game takes place in 2013. However, the game's manual uses the phrase "three weeks into the future," and the website's clock is always set three weeks ahead of the current time  — this puts forward the idea that the game takes place in an unspecific time and place, fitting with the game's setting of "Anywhere, USA." On top of this, radio host Johnny Riccaro mentions in the game that "the millennium's coming," which would make the possibility that the game is possibly set in 1999.
- Teddy Benavidez is arrested for heroin possession, aged 19.
- Chan Jaoming is arrested for heroin possession, aged 31.
- Lester Leroc is arrested for burglary: Illegal Entry with Criminal Intent, aged 37.
- Michael Graves is arrested for a criminal sexual act, aged 49.
- Dave Johnson is arrested for manslaughter, aged 21.
- Bozo is killed by police officers during a shootout.
- Ray Boccino is arrested for burglary, aged 23.
- Trey Stewart is arrested for possession of a controlled substance: Crack Cocaine, aged 16.
- Gerald McReary is arrested for conspiracy to commit extortion, aged 26.
- Dwayne Forge is arrested for possession of a controlled substance: Crack cocaine with intent to sell, aged 26.
- Terry Thorpe is arrested for manslaughter, aged 22.
- Tyrone Hancock is arrested for public lewdness, aged 37.
- Tony Prince is arrested for public lewdness, aged 41.
- Tom Rivas is arrested for coercion blackmail, aged 18.
- Jason Michaels is arrested for hijacking, aged 20.
- Luther Austin is arrested for public intoxication and disorderly conduct, aged 37.
- Bucky Sligo is arrested for armed robbery, aged 42.
- Angie Pegorino is arrested for Driving while Intoxicated, aged 38.
- Jim Fitzgerald is arrested for Production of Methamphetamine, aged 36.
- Clarence Little is arrested for possession controlled substance: Intent to Sell, aged 14.
- Merle Abrahams supposedly commits the murders of eight young men.
- Fabien LaRouche moves to San Fierro.
- Marvin Trill updates his website area53site.com on December 28th at 11:38 PM for the last time before going into hiding underground for ten years to avoid the Y2K disaster.