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Chelsea made four changes from the team that beat Stoke at the weekend as David Luiz replaced Gary Cahill in the centre of defence, Michael Essien started in favour of John Obi Mikel, Juan Mata came in for Raul Meireles and Daniel Sturridge took the place of Salomon Kalou in attack.
Napoli also made changes, but following their incredible 6-3 win over Cagliari at the weekend, only two changes were made to the team. Andrea Dossena was replaced by Christian Maggio and danger man Edinson Cavani returned to the starting line-up for Goran Pandev.
Chelsea opened the scoring through Didier Drogba, finding the net with his head in the first-half, and they doubled their lead on the night just after halftime as John Terry nodded in from a corner.
Napoli put themselves back in the lead on aggregate soon after as Gokhan Inler smashed an effort home on the edge of the area, but Frank Lampard restored their two-goal lead on the night as he scored from the penalty spot, and Branislav Ivanovic got the goal to send Chelsea through in extra-time.
The first chance of the match fell to Sturridge as he volleyed goalwards at an angle in the penalty area, but Morgan De Sanctis palmed it behind for a corner.
It didn't take long for Napoli to show their attacking ability, however. Inler played the ball into Ezequiel Lavezzi on the edge of the penalty area and after swivelling, he let rip, but Petr Cech made the save, if a little awkwardly.
The visitors were continuing to look extremely imperious in attack. This time it was Cavani who went close, getting on the end of Maggio’s low cross at the back-post, but much to the relief of the Chelsea fans the Uruguayan could only find the side netting, and Chelsea eventually made him pay.
After 27 anonymous minutes, Drogba gave the home team the lead. Ramires took up possession on the left wing and delivered an excellent ball towards the near-post for Drogba to throw himself at and nod down past De Sanctis.
Chelsea continued to control much of the action and went close to extending their lead just before halftime. Following a corner, Ramires found Luiz in space on the right side of the area, but the Brazilian’s low drilled cross was brilliantly cut out by Paolo Cannavaro, just ahead of Drogba, giving De Sanctis the opportunity to gather it to keep the score at 1-0 at halftime.
It didn't take long for the hosts to level the aggregate score after halftime, however. Napoli sloppily gave away a corner, and Terry rose highest to head the ball out of De Sanctis’ reach and double Chelsea’s lead on the night.
Chelsea’s two goal lead didn’t last long, though. With 54 minutes gone, Terry headed substitute Dossena’s cross out to the edge of the area, but only as far as Inler, who chested the ball under control and smashed a half-volley into Cech’s bottom right corner.
The Napoli goal hardly ushered in a new sense of urgency in the Chelsea performance, but Roberto Di Matteo did see fit the decision to bring on Fernando Torres, who had gone 25 matches for club and country without a goal.
A little later, Drogba again tested the former Sevilla goalkeeper. Ivanovic’s throw-in found its way to the Ivorian, who spun and volleyed with his left foot, but De Sanctis threw himself down to his right and tipped the ball round the post for a corner.
With 20 minutes left on the clock, the visitors came so close to levelling the score on the night. Camilo Zuniga linked well with Lavezzi and a slip from Ashley Cole allowed the Colombian to march into the area, but his shot was saved by the right hand of Cech, who did well to palm it away from the lurking Cavani.
Five minutes later, however, Chelsea won themselves a penalty and took a 3-1 lead on the night. From a corner, Ivanovic headed the ball onto the right hand of Dossena, with the referee rightly pointing to the spot, from where Frank Lampard buried his effort.
Clear-cut chances were few and far between after Lampard's penalty and the two teams were forced to play another half-hour of football as the aggregate score was tied at 4-4.
Following a few chances for Ivanovic and Torres in the opening half of extra-time, Chelsea got the goal to send themselves through just before halftime as the Serbian defender slammed a shot into the roof of the net after excellent work on the right from Drogba.
The second-half of extra-time was very nervy for the hosts, but after Drogba missed a golden opportunity in the dying moments, Chelsea held on despite pressure from their visitors and progressed to the next round.
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