1999 AFL first preliminary final

Essendon entered the match as heavy favourites, but Carlton recorded a narrow upset victory by one point.

After its Round 16 match, a 76-point loss against Essendon, Carlton sat tenth on the ladder,[2] and coach David Parkin publicly called his side a "B-grade team".

Then, during the week, Carlton president John Elliott attacked Essendon in media for having "cheated" its way to the 1993 premiership – a reference to the fact that Essendon had recently been found guilty of breaching the league's salary cap around that time.N 3, [7] Carlton kicked to the Punt Road end of the ground in the first quarter.

[12] Essendon had more opportunities to extend the lead shortly afterwards, but Lloyd, Fletcher and Dean Rioli all missed set-shots from inside 50m.

Essendon's resurgence and dominance in the third quarter came when the team began to win in the midfield, particularly through the efforts of Michael Long and Darren Bewick.

Carlton scored the next two goals after that – the first to Hamill, the second to Whitnall from outside 50m,[14] and in both cases assisted by Hogg – to regain the lead by 8 points early in time-on.

[10] Essendon attacked hard, but its forward thrusts were repeatedly repelled by Carlton's defence, including Koutoufides, who had dropped back.

Carlton cleared the ball forward, ending with a mark to Justin Murphy, who was able to run out the clock preparing for a set shot.

[15] Two moments in the match are best remembered: Anthony Koutoufides' final quarter, and Fraser Brown's last-minute tackle on Dean Wallis.

He had ten kicks, two handpasses, six marks and two goals for the quarter;[10][13] in a special analysis done for the game, Koutoufides would have earned 127 Champion Data ranking points for the quarter.N 5, [16] After the match, club legend (and later, president) Stephen Kernahan described Koutoufides' performance as "the greatest quarter of football ever played".

[16] Fraser Brown's tackle on Dean Wallis is widely remembered as the decisive single moment of the match.

[18] After Carlton had surrendered the lead in the third quarter, vice-captain Stephen Silvagni delivered an impromptu three-quarter time address to his team-mates.

[19] It was Essendon's second one-point loss in a preliminary final in just four years, after the Sydney Swans defeated them in 1996, courtesy of an after-the-siren behind to Tony Lockett.

[20] In the lead-up to the grand final during the week, Aaron Hamill was cited on video evidence for kneeing Dean Wallis in the head while the latter was on the ground during the third quarter.

Hamill was found guilty and the AFL Tribunal initially suspended him for two matches, which would have seen him miss the grand final.

Across the previous twenty years, the results of the rivalry – including the 1993 Grand Final, the close games and the controversies – had overwhelmingly favoured Essendon.