كتب : Omar AbdelAziz
An epic encounter at Stamford Bridge saw the hosts take an early lead through youngster Patrick van Aanholt, but Newcastle replied with three goals by Nile Ranger, Ryan Taylor and Shola Ameobi.
The Blues, mostly with their reserve team, were saved by two goals from Nicolas Anelka, before Ameobi stunned the crowd with a decisive 90th minute header.
At Anfield, Liverpool's dismal start to the season continued as they crashed out of the competition with a shootout defeat to fourth-division Northampton.
Milan Jovanovic's opener for the Reds was cancelled out by Billy McKay to force extra time, where Michael Jacobs scored, only to be denied by Liverpool's David Ngog.
However, Ngog missed his penalty, along with youngster Nathan Eccleston as Northampton grabbed a famous 4-2 victory.
Big-spenders Manchester City also joined Chelsea and Liverpool to the exit door after a 2-1 defeat at West Brom.
Holders Manchester United were the biggest winners as they came back from behind to thrash Scunthorpe 5-2, courtesy of a Michael Owen double.