The 1999 Brownlow Medal was the 72nd year the award was presented to the player adjudged the fairest and best player during the Australian Football League (AFL) home and away season. Shane Crawford of the Hawthorn Football Club won the medal by polling twenty-eight votes during the 1999 AFL season.
The count was notable in that it was the first and only time since the award’s inception in 1924 that it was held outside Melbourne. It was held in Sydney. The NSW Government paid $200,000 for the event but did anyone care.