Chelsea FC’s 5 greatest upsets of all time

(Photo by AMA/Corbis via Getty Images)
(Photo by AMA/Corbis via Getty Images) /
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(Photo by AMA/Corbis via Getty Images)
(Photo by AMA/Corbis via Getty Images) /

4. Chelsea vs. Napoli, Champions League Round of 16, 14 March 2012

Chelsea FC started the first leg of their Champions League Round of 16 tie against Napoli with Frank Lampard, Michael Essien and Ashley Cole on the bench. With some benefit of hindsight, Chelsea unsurprisingly lost 3-1 to the Italian side.

Two games later, after losing 1-0 to West Bromwich Albion, Chelsea sacked manager Andre Villas-Boas. Villas-Boas had been struggling to maintain the confidence of his star players as well as club ownership. The drama played out on the training ground and in Stamford Bridge’s office suites before spilling over into a series of ill-fated public moments.

The club appointed his assistant (and former Chelsea midfielder) Roberto di Matteo interim manager. The Blues won their first two games under di Matteo before Napoli visited London for the return leg. That night, Napoli teamed up with Chelsea to create 90 of the greatest minutes of football ever played in West London.

The match would have been memorable even as a standalone fixture, as any high-paced and aggressive 4-1 win at home would be. But knowing that Chelsea had to win by three goals to advance to the next round meant that taking a 3-1 lead in the 75th minute actually increased the tension around Stamford Bridge.

With the aggregate a 4-4 draw after 90 minutes, the match went to extra time. In the final minute of the first half of extra time, Didier Drogba teed up Branislav Ivanovic standing inexplicably wide open at the spot. Proving his reputation as one of the best striking-fullbacks in world football, Ivanovic one-timed the pass into the top of the net.

Fifteen minutes later, Chelsea sealed the comeback and were on their way to history.

Next: 3. Chelsea vs. Bradford City, FA Cup Fourth Round