Napoli put up a spirited display at Stamford Bridge, but capitulated in extra time to go out against Chelsea 5-4 on aggregate.
The Partenopei had a 3-1 first leg lead, although at the time Andre Villas-Boas was on the bench. He’d since been replaced by Roberto Di Matteo, who had won both his official games in charge going into this clash.
Didier Drogba and Daniel Sturridge were picked ahead of Fernando Torres and Solomon Kalou, while Raul Meireles was suspended. Napoli only missed Gianluca Grava and opted for Juan Camilo Zuniga rather than Andrea Dossena on the left. Walter Mazzarri had his touchline ban frozen on appeal so he could take part.
Visiting fans filled the away end and another 1,000 were peppered around the stadium in various different areas. There were reports that Napoli lodged a protest with UEFA as the temperature in their locker room was turned up far too high and it took over 30 minutes to fix the problem.
Sturridge had the first shot after five minutes, well palmed away at the near post by Morgan De Sanctis. At the other end, Marek Hamsik spun round and Petr Cech stuck out a leg to beat it away. Napoli went on the counter and Christian Maggio rolled across for Cavani to hit the side-netting at the back post.
Ezequiel Lavezzi also had a chance on 14 minutes, springing the offside trap round Ashley Cole for Cech to parry from close range. Moments later, Cech was at full stretch to prod a scuffed Hamsik effort off target. Chelsea had the ball in the net, but the flag had already been raised for a Sturridge offside position, while Zuniga ballooned over.
However, Chelsea did take the lead in one of their only scoring opportunities. Drogba’s diving header from the Ramires cross flew into the near bottom corner, as the Ivory Coast striker got in front of Salvatore Aronica. Di Matteo’s celebrations were so passionate that he slipped and almost fell flat on his face.
A Sturridge ball flashed across the face of goal and was intercepted just before Drogba could tap in at the back post. From that corner, Napoli went on the counter and Cavani’s angled drive was wide. More bad news for Mazzarri, as Maggio limped off for Dossena, moving Zuniga to the right flank. Michael Essien’s daisy-cutter whistled wide, as did a deflected Lavezzi snapshot.
Aronica intercepted a dangerous Drogba cross for Sturridge in the six-yard box, then from the corner David Luiz appeared to have beaten De Sanctis with an angled cross, but Paolo Cannavaro stopped it reaching Drogba and prodded it back into the grateful arms of his goalkeeper.
It was the worst possible start to the second half for Napoli, as Hugo Campagnaro gave away a cheap corner from which an unmarked John Terry nodded across De Sanctis into the far top corner to give Chelsea the 2-0 lead on the night and the aggregate lead on away goals.
The Partenopei reacted strongly and got their away goal with some style. Gokhan Inler took down a poor Terry clearance with his chest and smashed a right-foot volley from the edge of the box that left Cech with no chance. With this situation, Chelsea needed a 3-1 win to force extra time, so they threw on Torres for Sturridge.
De Sanctis needed a fantastic reaction save when the Branislav Ivanovic shot took a deflection from seven yards. Moments later the goalkeeper needed another wonderful interception, as he flew to palm a Drogba turn and volley round the far post.
Napoli also threatened when Zuniga ran on to a Cavani backheel flick for the strike parried by Cech at the near stick. Zuniga risked an own goal with a horribly scuffed clearance on a corner, but got away with it.
Chelsea were awarded a penalty for Dossena’s handling offence when charging down an Ivanovic header. Frank Lampard converted despite De Sanctis getting the right angle to make it 3-1 and completely even on aggregate and away goals.
David Luiz charged down a Cavani header, then Ashley Cole did the same on the Hamsik follow-up. Lavezzi just couldn’t get his head to a whipped in Hamsik cross from seven yards. Walter Gargano even tried to score from distance with a blast that landed on the roof of the net.
A cross flew across the face of goal and Drogba went down in a tussle with Aronica, but they seemed to be wrestling each other. With the tie all square on aggregate at the final whistle, it went to extra time.
Ivanovic’s free header from a corner whistled wide, as did a well struck Hamsik volley. There was a moment of absolute panic when De Sanctis rushed off his line and misjudged the bounce which went right over him, but Torres also seemed surprised and only fired on to the side-netting of an open goal.
A Torres looping header landed on the roof of the net, but Chelsea did break through just before the end of the first half of extra time. Drogba did brilliantly to spin round and pull back across the face of goal for Ivanovic to smash it first time under the bar.
Goran Pandev replaced Hamsik and Edu Vargas came on for defender Aronica, as Napoli would go through if losing 4-2 on the night thanks to away goals. De Sanctis grabbed a deflected Torres effort from distance and Drogba scuffed his volley wide on the counter. The Partenopei looked very tired and could not find that second away goal.
Chelsea 4-1 Napoli aet (5-4 on agg)
Scorers: Drogba 28 (C), Terry 47 (C), Inler 55 (N), Lampard pen 75 (C), Ivanovic 104 (C)
Chelsea:Cech; Ivanovic, Terry (Bosingwa 98), David Luiz, A Cole; Ramires, Essien; Lampard, Juan Mata (Malouda 95), Sturridge (Torres 63); Drogba
Napoli: De Sanctis; Campagnaro, Cannavaro, Aronica (Vargas 110); Maggio (Dossena 36), Gargano, Inler, Zuniga; Hamsik (Pandev 105), Lavezzi; Cavani
Ref: Brych (GER)
Think you know your Italian football? Share your knowledge, tips and comments to win cash prizes in OLBG's tipster competition  - £5,000 monthly.