Events concerning the Grand Theft Auto series in 1999.
- April 29: Grand Theft Auto: London 1969 is released for the PlayStation.
- May 25: Grand Theft Auto: London 1969 is released for the PC.
- June 1: Grand Theft Auto: London 1961 is released for the PC.
- October 22: Grand Theft Auto 2 is released.
- November 15: Grand Theft Auto 1 is released for the Game Boy Color.
- Eldon Samuel III, who in March 2014 murdered his father and brother after allegedly idolising Trevor Philips from Grand Theft Auto V, would have been born in either 1999 or 2000.
The events of Grand Theft Auto 2 take place.
- Bilovski (killed by a backfiring rocket launcher delivered by Claude Speed)
- Billy Bob Bean (killed by Claude Speed)
- Uno Carbine (killed by Claude Speed)
- Flambo Cortez (killed by Claude Speed)
- Doctor Cubana (killed by Claude Speed on orders from Trey Welsh)
- Elmo (killed by Claude Speed)
- Jerkov (killed by Claude Speed)
- Fat Boy Jim (killed by Claude Speed on orders from Montana Shane)
- Dr. LaBrat (killed by Claude Speed)
- Sunbeam (killed by Claude Speed)
- Red Valdez (killed by Claude Speed)
- Trey Welsh (killed by Claude Speed)
- Johnny Zoo (killed by Claude Speed)
- The car company Maibatsu comes out with a 12 seat SUV called the Maibatsu Monstrosity. The car is advertised having a submarine feature.
- Bozo (killed in a shootout with Liberty City Police Department)
- Eight unnamed people near Sandy Shores.
- Luther Austin is arrested for public intoxication and disorderly conduct.
- Teddy Benavidez is arrested for heroin possession.
- Jim Fitzgerald is arrested for unlawful manufacturing methamphetamine.
- Dwayne Forge is arrested for possessing a controlled substance with intent to sell.
- Michael Graves is arrested for a criminal sexual act.
- Chan Jaoming is arrested for heroin possession.
- Dave Johnson is arrested for manslaughter.
- Lester Leroc is arrested for burglary.
- Angie Pegorino is arrested for driving while intoxicated.
- Gay Tony is arrested for public lewdness.
- Playboy X is arrested for possessing crack cocaine.
- Eight people go missing near Sandy Shores in Blaine County, San Andreas, having been murdered by "The Infinity Killer" Merle Abrahams. Abrahams' is later arrested and sentenced in the same year, after his home had been burnt down by the residents of Sandy Shores. He was later sent to Bolingbroke Penitentiary.
- Fabien LaRouche moves from France to San Fierro.
- Gay Tony opens the Hercules nightclub in Westminster, Liberty City.
- Henrique Bardas and Armando Torres being hitting on college girls in Northwood, Liberty City.