During that period, the Bombers won 12 of the 14 meetings between the two sides as they flexed their muscle at the top of the AFL ladder.
With wins against one of their traditional rivals being so sparse, Collingwood fans had reason to celebrate their 16-point win over the Dons in round 22, 2003.
Watch highlights of the match on CTV in the media player above.
But the win had greater implications than simply notching a memorable win over their old foe.
Read Glenn McFarlane's take on the famous victory.
The victory meant that the Magpies secured second place on the ladder at the end of the home and away season and in turn locked in the vital double chance and a home Qualifying Final.
But the four points weren't handed to them on a silver platter.
Essendon had their own September-related concerns, and banged on five goals to two in the second quarter to lead by six-points at half time.
It took gutsy performances from Josh Fraser (20 possessions, 24 hitouts, one goal), Shane Woewodin (23 possessions, nine tackles, two goals) and captain Nathan Buckley (27 possessions, two goals, seven marks) to ensure that Collingwood could sew up the coveted home final.
Although the season ended with a disastrous loss to the Brisbane Lions in the Grand Final, the round 22 victory over the Bombers was one of several games that year that left Pies fans believing that 2003 would be their year.
Collingwood 3.3, 5.7, 9.9, 12.11 (83)
Essendon 1.3, 6.7, 8.9, 9.13 (67)
Goals - Collingwood: Buckley 2, Rocca 2, Woewodin 2, Tarrant, Burns, Fraser, Lonie, O'Bree, Cole
Essendon: Haynes 2, Lloyd 2, Solomon 2, McPhee, McVeigh, Jacobs
Best - Collingwood: Fraser, Woewodin, Buckley, J.Cloke, Tarrant, Johnson, Clement
Essendon: Hird, Rioli, Fletcher, Solomon, Welsh, McVeigh
Brownlow Medal: 3. S.Woewodin (Coll), 2. J.Hird (Ess), 1. N.Buckley (Coll)
