The 1999 Preakness Stakes was the 124th running of the Preakness Stakes thoroughbred horse race.

Charismatic, who was jockeyed by Chris Antley, won the race by one and one half lengths over runner-up Menifee.

The race was run over a fast track in a final time of 1:55.32.

[1] The Maryland Jockey Club reported total attendance of 116,526, this is recorded as second highest on the list of American thoroughbred racing top attended events for North America in 1999.

[2] The 126th Preakness Stakes Payout Schedule