A closer look at Napoli manager Carlo Ancelotti’s history with Liverpool

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It is not inconceivable that Carlo Ancelotti could have been sitting in the Liverpool dugout for Tuesday night’s crucial Champions League showdown against Napoli.

Ancelotti was a serious consideration to replace Brendan Rodgers in 2015 before the Reds instead plumped for Jurgen Klopp and the rest is European football history.

Nevertheless, much of Ancelotti’s history as both a player and manager is remarkably intertwined with the club he will try to knock out of the competition. Press Association Sport investigates.

Roma v Liverpool, 1984 European Cup final

Ancelotti led Roma into the European Cup final at the Stadio Olimpico but his illustrious playing career was beset by knee injuries and he was forced to watch from the bench as his side were beaten by Liverpool on penalties – Bruce Grobbelaar’s famous wobbly legs and all.

AC Milan v Liverpool, 2005 Champions League final

Ancelotti suffered more woe at the hands of the Reds on that famous night in Istanbul, when his AC Milan side skated into a 3-0 lead only to find themselves on the receiving end of an astonishing second-half comeback. Ancelotti described his side’s capitulation as “six minutes of madness” and added: “I think we played a marvellous final. We lost without deserving to lose.”

AC Milan v Liverpool, 2007 Champions League final

Still in charge of Milan two years later, Ancelotti revealed his players were desperate for the opportunity of revenge. “I wanted them and the lads wanted them,” Ancelotti wrote in his autobiography.

“It was too beautiful to be able to take revenge for Istanbul two years before.” Two goals from Filippo Inzaghi proved enough for Ancelotti to get what he wished for with a 2-1 win.

UEFA Champions League Final: Liverpool v AC Milan

Liverpool v Chelsea, Premier League 2010

Ancelotti’s Chelsea side all but wrapped up the Premier League title with their vital win at Anfield in 2010, in a match made famous for Steven Gerrard’s slip.

Prior to the game Ancelotti revealed he had never previously visited Anfield. “I’ve played against Liverpool many times in my career,” he said. “Liverpool have a fantastic history. When I hear the fans singing ‘You’ll Never Walk Alone’, it is a fantastic emotion, even if I’m not a Liverpool fan.”

Liverpool v Chelsea - Premier League

Liverpool v Real Madrid, 2014 Champions League

By now boss of Real Madrid, Ancelotti orchestrated a dominant 3-0 win for his side at Anfield, with all three goals coming in the first period.

Asked whether his mind had slipped back to the 3-0 lead his Milan side had held in the 2005 final, Ancelotti laughed: “I forgot this. I told the players that in football anything can happen. I know very well these Liverpool supporters stay close to their team, so I told my players to stay focused.”

Carlo Ancelotti

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