Losing the unlosable.

That’s how Essendon legend Matthew Lloyd described the Bombers’ shock 1999 preliminary final loss to arch-rival Carlton.

Despite the Dons finishing first on the ladder, five places higher than its penultimate finals-week foe, it would be the Blues who would march on to face eventual premier North Melbourne in the Grand Final.

The one-point defeat is best remembered for the desperate tackle from Carlton’s Fraser Brown on Essendon backman Dean Wallis with 38 seconds to go to deny the Bombers one last chance to grasp victory.

It’s a moment which haunts Dons fans to this day, given Essendon held a 17-point lead in the final term having entered the game as heavy favourite.

That result condemned Essendon to one of the most embarrassing losses in club history, with champion defender Sean Wellman recounting then-senior coach Kevin Sheedy telling the playing group in the aftermath that 'You’ve just gift-wrapped the premiership to North Melbourne’.

Dean Solomon shows his anguish after the Bombers' preliminary final loss to Carlton. (Photo: AFL Photos)

Football history has shown heavy or unforgiveable finals losses can often affect the psyche and confidence of a playing group, something which the Essendon coaching staff was keen to avoid.

This belief in healing the wounds of such a loss resulted in a remarkable story of how the players had to swallow their pride and endure humiliation to eventually fuel the success they enjoyed the following year.

“We had two or three days of drowning our sorrows and then on the Wednesday of Grand Final week, Kevin Sheedy sends a message out saying the club has purchased Grand Final tickets for us to watch,” Lloyd told The Bombers: Stories of a Great Club.

“There were North supporters and Carlton supporters grabbing their throats saying ‘You’ve choked, you should be here and you’re not’. It was hard watching.”

Having gone through the myriad of emotions that accompany watching a game they should have been in, the players were then led across the road from the MCG to an unannounced location.

Waiting for them was what Lloyd said changed the team’s thought process from one of self-pity to hunger for redemption.

“We get halfway through the last quarter and Kevin Sheedy says, ‘Alright, boys, get up and follow me’,” Lloyd said.

“We’re walking out of the ground and you can imagine what we were copping as we were walking out.

“We walked across the road to just near the Hilton Hotel, there was a restaurant and Robert Shaw, Sheedy’s assistant coach, was there waiting for us. He handed out folders (to everyone) and said, ‘This is where our 2000 campaign starts’.

“‘Shawry’ had in the folder the four teams we needed to beat in 2000 to win the premiership.

“[In there] was Melbourne, who we played in the Grand Final, Carlton, who we played in the preliminary, and North Melbourne, who we smashed in the first final.”

That preparation from Shaw was a monumental driver in helping Essendon achieve a record-breaking year in 2000.

Former Essendon assistant coach Robert Shaw. (Photo: AFL Photos)

The Dons went famously close to being undefeated the entire year, only losing one home-and-away game in round 21 to the Western Bulldogs by 11 points.

All of the side’s domination in that season can be traced back to the ’99 Grand Final day and the events that transpired from there.

“It was an amazing coaching performance where they changed our mindset from dwelling on it for a month to the 2000 season starts now," Lloyd said.

“They brought a training camp forward and we had an intense (period) at Essendon Grammar, and by the time round one came, we were as driven and hard (as ever).

10:01 Mins
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“We didn’t sing the club song for any victory (in 2000). There was one win that was going to do it for us, and that was the Grand Final.”

The Dons’ ‘99 prelim story features in episode seven of The Bombers: Stories of a Great Club, which will air at 7:30pm AEDT on Tuesday exclusively on Fox Footy and Kayo. Episode eight will begin at 8pm. This next instalment will wrap up the docuseries.