September 18, 1999….

Because Steve Bracks pulling Jeff Kennett’s pants down to win the State Election was the second-biggest upset in Victoria that day:

Essendon, after finishing top and winning 14 out of 15 games leading into the Preliminary Final: 14.19-103

Carlton, 5/1 outsiders after crawling into the Top 8 and losing their first final by 73 points: 16.8-104

Of course, Carlton went on to lose to North Melbourne the next week, and the Blues haven’t played in a Grand Final since… then again, neither have North.

Some other great historical notes from the game:

It was the third time Essendon had lost a Final by 1 point in the span of four seasons, two of them being Preliminary Finals (1996 & ’99).

The Bombers have played in 5 finals decided by 1 point, losing every single one of them (1947 GF, 1986 EF, 1996 QF, 1996 PF, 1999 PF).

Anthony Koutafides’ stats in what many have described as not just the greatest final quarter ever played, but perhaps the greatest quarter every played by a single player: 10 kicks, 2 handballs, 6 marks, 2 goals, 127 ranking points, playing in every part of the ground.

25 years later, it remains Carlton’s last win in a Preliminary Final – The Blues have played in only 2 since 1999 (2000 & 2023).

It was the first time since North Melbourne in 1983 that the minor premier had missed the Grand Final… 1983 being the old days of the Top 5 Finals system.

It was Carlton’s first win against Essendon since 1997… they had also lost to the Bombers by 1 point on Easter Monday of 1998, and lost both games in 1999 by convincing 39 (Round 1) and 76 (Round 16) point margins.

Mark Mercuri and Blake Caracella combined to kick 7 behinds without a goal… Mercuri kicked the last score of the game to make the margin 1 point with just under a minute remaining.

Despite winning a Premiership and a Best & Fairest for Carlton, Fraser Brown will forever be remembered for his monster tackle on Dean Wallis with 30 seconds to go that all but sealed the result:

Aaron Hamill was suspended for 2 games for kneeing Dean Wallis in the head, meaning he would’ve missed the Grand Final, but Carlton employed a biomechanics expert at the AFL Appeals Board to elaborately prove that the contact was accidental, a tactic that seemingly worked as Carlton’s appeal was upheld and Hamill played the next week… Hamill admitted years after the fact that he had done it intentionally, and that the biomechanics expert was simply there to bore the Appeals Board.

The next week, Essendon players attended the Grand Final on Kevin Sheedy’s orders (The Bombers’ Reserves team were also playing in the Grand Final) and left before the final siren.

The ’99 Prelim, and the Grand Final attendance, was a major source of motivation for Essendon’s all-time great 2000 season, winning the pre-season competition undefeated, the minor premiership with just 1 defeat from 22 games, then winning all 3 Finals to win the Premiership, defeating Carlton by 48 points in the Preliminary Final along the way.

Carlton going to the Grand Final from 6th after losing their first final by 73 points against the Brisbane Lions was the final nail in the coffin for the McIntyre Top 8 system, in which the two lowest-ranked teams were eliminated in Week One, allowing for results like Adelaide’s 1998 flag (From 5th after losing by 8 goals in Week 1) and Carlton’s ’99 Grand Final run.

The system was replaced by the current Top 8 system for the 2000 season (Which the ARL had used in 1995 and 1996), with the Top 4 teams being given a double chance.