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 time since the award's inception in 1924 that it was held outside Melbourne.