A stunning Patrick Kluivert goal headed Newcastle into Monday's FA Cup sixth round draw in a bizarre tie at St James' Park.
Chelsea ended the match with only nine players after gambling on three half-time substitutions that backfired badly as Jose Mourinho suffered only his third defeat as Chelsea boss and saw his quadruple dream in tatters.
Just seconds into the second half, the Premiership leaders were down to ten players when Wayne Bridge was carried off with a suspected broken left ankle.
Then in time added on, goalkeeper Carlo Cudicini was red carded for a foul on substitute Shola Ameobi as Chelsea ended with William Gallas and Damien Duff clearly carrying leg injuries.
Newcastle, who had not beaten Chelsea in any cup competition since 1932, got
off to a dream start with a goal in the fourth minute following a superb passing movement.
It went from the left of the park to the right and switched back again and was stunningly finished by Kluivert.
The move was finalised when Stephen Carr switched inside to Nicky Butt – who had started the move - who swept the ball wide to Laurent Robert. The fans' favourite then produced a stunning cross that was bettered only by Kluivert's header which gave Cudicini no chance.
The roof almost came off St. James' Park in a stunning opening 20 minutes as Newcastle's passing play hit top gear.
But, Newcastle could not capitalise on the situation in terms of goals and this ultimately allowed Chelsea back into contention.
It was not until the 23rd minute that Chelsea managed their first effort and Mateja Kezman's header went well wide.
Kezman - whose only Chelsea league goal came from the penalty spot against Newcastle - was then denied number two by the woodwork.
Jean Alain Boumsong was caught appealing for offside to no avail and although he got back, Tiago's cross deflected off him into the path of the Serb who lifted the ball over Shay Given and on to the underside of the bar before Newcastle got it away.
It was not until the 27th minute that Chelsea troubled Given for the first time with a shot on target with Given sprawling to his left to keep out the impressive Jiri Jarosik's low drive.
Mourinho showed his intentions at the break as he hauled off Joe Cole, Tiago and Geremi and sent on big guns Eidur Gudjohnsen - seven goals in his last seven games against Newcastle - Duff and Frank Lampard.
Yet within seconds of the restart, Chelsea were down to ten men when they lost England defender Bridge who was taken to Newcastle General Hospital with a suspected break to his left ankle.
Alan Shearer slid in for a legitimate challenge to force a throw in, but at the same time Bridge went over the top of the striker and sustained the injury that saw play held up for several minutes as the former Southampton man was stretchered from the pitch.
It meant that Chelsea were down to ten men for the remainder of the second half, but you could hardly tell as the Londoners dominated the game.
Chelsea were magnificent as they pressed forward and Gudjohnsen twice forced Given into saves.
But the alarm bells once again rang on the Chelsea bench when Duff was injured. He chased back brilliantly to keep out Carr but collided with Cudicini and limped for the remainder of the half.
Newcastle were forced to play second fiddle against the gallant Chelsea side until a dramatic time added on.
First Glen Johnson's clearance almost flashed into his own net before Cudicini saw red for bringing down Ameobi - the second time in his career he had been sent off by Mark Halsey.
With Chelsea expecting Kluivert to shoot from the resulting free-kick, Robert raced in to bring a brilliant block from stand-in keeper Johnson with what was only Newcastle's second shot on target.