More than a decade on, Jess Sinclair still rates the loss as one of the most heartbreaking he's ever been involved in.
Of course he's talking about Round 16 in 2001 when North Melbourne surrendered a 69 point lead early in the second quarter against Essendon and lost by 12 points.
North fans will say it was one of the most remarkable games in AFL history, for all the wrong reasons.
Sinclair recalled the growing positivity of the group leading into the game with the Roos’ season getting back on track after an indifferent first 12 rounds.
"That was my first year at the footy club and looking back, our list was unbelievable. We just couldn't get everyone on the park at the same time. Duck (Wayne Carey) was injured and suspended and we just needed to get our best 22 out on the ground.
"Going into that game, it seemed that every week beforehand was a finals-on-the-line type of game. We really did get ourselves up for the Essendon game even more so and everything came together in the first quarter."
And what an understatement that was. Against a side that had won 37 out of its last 40 games, North slammed on twelve goals to just two.
Recap the first quarter by pressing PLAY above
"It was one of those quarters where everything we did went right," Sinclair continued.
"Everyone just played out of their skins in the first quarter. From the memories I have of that game, I remember Boomer Brent Harvey and Sav (Saverio Rocca) just having the ball on a string. We were on top in pretty much every area.”
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"After we did kick all those goals in the first quarter, we knew that they were still regarded as the ‘Invincibles’, they were still Essendon. Heading into the quarter-time break, I remember not actually feeling safe. With any other team you'd think the game was in the bag but you just get the feeling that looking around the group we were all thinking, ‘they might come back at us here’."
Despite not having watched the game for a long time, when quizzed about the last three quarters Sinclair immediately named Jason Johnson (31 touches, 4 goals) and Matthew Lloyd (9 goals) as Essendon’s chief destroyers - coincidentally they were the two Bombers who received Brownlow votes on the day.
While he described the loss as 'deflating' and 'shattering' among other things, Sinclair still has some positive memories of the day.
"The beauty of it was that it was good old-fashioned footy. There wasn't any flooding, or a press, or something like that. Everyone played in their position, it was long, direct footy and contest to contest. That's what a lot of people like to see."
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"In my time at the club with guys like Boomer and Shannon Grant, regardless of where each club was sitting, we always got up for an Essendon game."
"They didn't beat us for a long time and it was definitely something that we prided ourselves on."
As the winning streak over Essendon since that game stretched multiple years, the feeling between the two clubs has intensified. Games between the two were regularly physical and Sinclair explained why.
"Now that I'm not playing anymore, I can say that we absolutely hated Essendon. I think the feeling's mutual as well and it goes back a long way before I was ever at the club.
Since he stepped away from AFL, Sinclair has kept himself busy with other pursuits. In addition to his own clothing line, he's involved in the fighting game.
"I've got a mixed martial arts company that I started up two years ago. It's called Australian Fighting Championship (AFC) and our next event is in Geelong on the 14th of April. A few of the North boys make their way down to our events; Hamish McIntosh actually came down to our most recent one."
But his thoughts never stray too far from Aegis Park and he'll be watching keenly on Saturday night.
"I dare say the boys will get themselves up again this weekend and hopefully they can have a win."
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Essendon 2.3 (15), 12.4 (76), 19.8 (122), 27.9 (171)
Kangaroos 12.1 (73), 16.1 (97), 22.4 (136), 25.9 (159)
Goals: Essendon - Matthew Lloyd 9, Jason Johnson 4, Blake Caracella 3, James Hird 2, Cory McGrath 2, Gary Moorcroft 2, Mark Bolton 1, Chris Heffernan 1, Danny Jacobs 1, Mark Johnson 1, Adam Ramanauskas 1
North Melbourne - Corey McKernan 5, Saverio Rocca 4, Brent Harvey 3, Byron Pickett 3, Jess Sinclair 3, Shannon Grant 2, Brady Rawlings 2, Matthew Burton 1, David Teague 1, Shannon Watt 1
Leading possession winners: Essendon - Jason Johnson 31, Blake Caracella 28, James Hird 22
North Melbourne - Brent Harvey 27, Shannon Grant 26, Adam Simpson 25
Brownlow Medal: Jason Johnson (ESS) 3, Matthew Lloyd (ESS) 2, Corey McKernan (NM) 1
