The 1999 finals series of the Australian Football League began on 3 September 1999 and ended with the 103rd AFL Grand Final at the Melbourne Cricket Ground on 25 September 1999 contested between the Kangaroos and Carlton. The Kangaroos, (formerly and later known as North Melbourne), emerged victorious to claim their fourth VFL/AFL Premiership.
The top eight teams on the home and away rounds (regular season) ladder qualified for the Finals Series.
Essendon finished one game clear on top of the ladder with 18 wins, and thus claimed its 15th minor premiership. The Kangaroos were second with 17 wins, trailed by the in third place with 16 wins, but with the best percentage of any team in the Eight. In fourth place were the who finished with 15 wins and a draw. The following three teams (, and ) finished with 12 wins each, separated by percentage. (with 11 wins) rounded out the Eight. <br/ >
According to the McIntyre final eight system, this was how the first week of finals matches were arranged:
The 1999 finals series was probably best remembered by the preliminary final boilover, in which upset minor premier Essendon by one point at the MCG, which qualified them for an unexpected Grand Final appearance against the Kangaroos.
The 1999 AFL season would also be the last season which used the McIntyre system. It was replaced the following year with the AFL final eight system.
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|- ! Home team ! Score ! Away team ! Score ! Venue ! Attendance ! Date |- bgcolor="#FFFFFF" | | 15.10 (100) | | 8.8 (56) | MCG | 31,476 | Saturday, 4 September
|- ! Home team ! Score ! Away team ! Score ! Venue ! Attendance ! Date |- bgcolor="#FFFFFF" | | 20.18 (138) | | 8.17 (65) | The Gabba | 26,112 | Saturday, 4 September
|- ! Home team ! Score ! Away team ! Score ! Venue ! Attendance ! Date |- bgcolor="#FFFFFF" | | 18.15 (123) | | 7.12 (54) | MCG | 57,687 | Sunday, 5 September
|- ! Home team ! Score ! Away team ! Score ! Venue ! Attendance ! Date |- bgcolor="#FFFFFF" | | 10.10 (70) | | 18.16 (124) | MCG | 55,682 | Saturday, 11 September
|- ! Home team ! Score ! Away team ! Score ! Venue ! Attendance ! Date |- bgcolor="#FFFFFF" | | 19.12 (126) | | 10.13 (73) | The Gabba | 24,045 | Saturday, 11 September
|- ! Home team ! Score ! Away team ! Score ! Venue ! Attendance ! Date |- bgcolor="#FFFFFF" | | 19.9 (123) | | 11.12 (78) | MCG | 61,031 | Friday, 17 September
|- ! Home team ! Score ! Away team ! Score ! Venue ! Attendance ! Date |- bgcolor="#FFFFFF" | | 14.19 (103) | | 16.8 (104) | MCG | 80,519 | Saturday, 18 September
|- ! Home team ! Score ! Away team ! Score ! Venue ! Attendance ! Date |- bgcolor="#FFFFFF" | | 19.10 (124) | | 12.17 (89) | MCG | 94,228 | Saturday, 25 September