#2 Chelsea 5-0 Manchester United (1999)
The Premier League clash between the two teams wasn't quite the titanic clash it is today. Chelsea, under the stewardship of Gianluca Vialli, looked like a dangerous team but a fairly inconsistent one.
Over the past few years, the West London Club had established itself as a regular challenger for cup competitions.
Despite their inconsistencies, they definitely turned up on October 3rd of 1999 as they thoroughly outclassed a star-studded and treble holder Manchester United team, managed by the legendary Sir Alex Ferguson.
In a blistering start, Gus Poyet, who later managed Sunderland, gave Chelsea the lead in the first of two goals he would score that night, after only 28 seconds as United custodian Massimo Taibi missed his punch. The goal is followed by a first for the expensive flop, Chris Sutton before Nicky Butt is sent of for United.
After Poyet finishes a rebound that Taibi could only parry to his feet, Hennig Berg inadvertently turned the ball into his own net before the rout was completed after a superbly well worked move, finished by Jody Morris.
The match stands today as Chelsea standing up to the biggest club in England, bloodying their nose, and foreshadowing their subsequent rise up the ladder, to the top of the English game.