The 1999 AFL Premiership season was the 103rd annual season of the VFL/AFL league contested between the 16 teams of the competition. Set to determine the premiers of the 1999 year, it was won by the second placed Western Bulldogs, their third in a row and fourth overall.
Sydney full-forward Tony Lockett overtook Gordon Coventry's 60 year old record for highest number of goals kicked by an individual VFL/AFL player, booting his 1300 goal against Fremantle at the SCG in round 7.
Essendon's first quarter score of 16.3 (99) against Collingwood in round 4 stands as a league record for the highest score kicked in the first quarter, and an overall club record for the Essendon Football Club. The final margin at the end of the game (33.11.209 to 7.14.56) stands as the 16th widest margin in the history of the league and the equal 20th highest score.
Both Waverley Park and Victoria Park hosted their final senior VFL/AFL games on round 22, the former stadium having served the league since 1970, and the latter having served as a Collingwood home ground since their inception into the VFA in 1892. They would go onto be replaced by Colonial (Docklands) Stadium in the year 2000.
In order to finish within the final eight (and thus secure a finals berth), Hawthorn needed to defeat Fremantle by more than 100 points in order to climb higher than Brisbane based in percentage. They ultimately won 23.13.151 to 5.6.36, an 115 point victory which relegated Brisbane to number nine on the ladder, and presented Hawthorn a shot at the premiership.
With their final round home-and-away victory against the Western Bulldogs, Essendon finished the season on top of the ladder as minor premiers, the 15th time in their history.
At the bottom of the ladder, Collingwood won the wooden spoon, having won only two games for the entire season (both against Melbourne) in round 2 and 19, the third wooden spoon in their history.
Finishing his career off with the Coleman, Tony Lockett kicked the most goals in the 1999 season, his 7 goal haul in the final two rounds lifting him to 98 goals for the entire home-and-away year.
Two 'best-and-fairest' players won the Brownlow at the end of the 1999 season; the West Coast forward Ben Cousins and the Western Bulldogs midfielder Scott West, both of whom ended with 26 votes during the Brownlow tallying.