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He did a terrific job as interim manager, but if anything, Roberto Di Matteo only made his task harder as permanent manager by winning the Champions League.
After their incredible triumph in last season's Champions League, it would've been difficult for the Italian to emulate his success. The only way to do that would be winning several of the eight competitions Chelsea were due to enter.
Unfortunately, things didn't go quite as planned. The Blues were drawn into a tough group in the Champions League, with Serie A champions Juventus and Ukrainian giants Shakhtar Donetsk providing quite a test for the reigning champions, while minnows Nordsjaelland from Denmark were making their debut.
After leading Juventus 2-0 at Stamford Bridge thanks to a stunning double from Oscar, qualification seemed well within their grasp from the opening game. However, two late goals from Arturo Vidal and Fabio Quagliarella ensured the Antonio Conte's side picked up a point, which would prove crucial.
Defeats against Shakhtar and Juventus away ultimately cost them a place in the group stage and Di Matteo his job, as he was brutally sacked by Roman Abramovich after the 3-0 defeat to the Old Lady. Despite a 6-1 thumping of Nordsjaelland on the final matchday, their slim chances of qualifying had gone as Juventus won 1-0 against Shakhtar at the Donbass Arena, sending both sides through.
Entering at the semifinal stage, they swept Mexican side Monterrey 3-1 before facing the Copa Libertadores holders Corinthians, from Brazil, in the final. A poor game in Yokohama saw Jose Paolo Guerrero strike a late winner to defeat the Blues, and a disappointing trip was capped by Gary Cahill's sending off for lashing out at Emerson in frustration. The Blues were coming home empty-handed.
The West London club had a bumpy ride ahead in the Europa League too, with trips to Romania, Czech Republic, Russia and Switzerland on their new yet unexciting journey. And yet somehow, despite several injuries and suspensions, the Blues managed to reach their second consecutive European final after overcoming Swiss outfit FC Basel 5-2 on aggregate.
Awaiting them were familiar foes Benfica, the Portuguese team who Chelsea had faced in last season's Champions League semifinal. And after a hard-fought final, it was Fernando Torres who broke the deadlock, brilliantly rounding goalkeeper Artur. However, it was Oscar Cardozo's penalty which leveled the tie.
As the clock was ticking towards extra-time, Branislav Ivanovic rose brilliantly to direct a looping header into the net, and send Chelsea fans into raptures. Rafa Benitez had done it—he had become the first manager to win the UEFA Cup/Europa League with two different clubs.
A silver lining to what could have been a season to forget for Chelsea.