Carlo Ancelotti in unfamiliar territory of derby underdog as Everton aim to cross growing Merseyside gulf

Going into a derby as an underdog will be a strange experience for Carlo Ancelotti. Throughout most of his career, the Everton manager has been in charge of clubs that were at least equal to their neighbours and generally more dominant. Against Liverpool at Anfield on Sunday the Italian will get to feel what it is like to be a second-class citizen in the battle for local pride.

Ancelotti’s task in the 235th Merseyside derby is not only to guide Everton into the fourth round of the FA Cup but to beat the unbeatable. Jurgen Klopp’s team have left even Manchester City by the wayside this season and Everton are trailing so far in the distance that it is embarrassing. Liverpool are 33 points clear of their neighbours – 11 victories ahead with a game in hand just 20 matches into the campaign. Anfield houses the Champions League and Club World Cup trophies while Goodison has not had a sniff of silverware for a quarter of a century. In the quest for parochial superiority, this appears to be a mismatch of epic proportions. But Ancelotti cannot be discounted. He has won some of the most epic derbies in history.

During his time at Milan, the 60-year-old was locked in a struggle for supremacy with

Internazionale and did not have it all his own way. Inter won four consecutive Serie A titles during the final seasons of Ancelotti’s tenure as the balance of power in the city swung away from the Rossoneri in the wake of the Calciopoli scandal. Milan kept their status as the San Siro’s leading club by winning two Champions League finals under Ancelotti, however. Their route to the first of those victories, the 3-2 win over Juventus on penalties at Old Trafford in 2003, included two of the most significant derbies in European history. Milan and Inter met in the semi-final and after a 0-0 draw in the first game, Ancelotti’s team secured a 1-1 draw in what was nominally the away leg to seal a place in the final.

Events in Spain 11 years later would eclipse that Milanese showdown. Domestically, Atletico Madrid – who will always be fated to be the second club in the Spanish capital – were much better than Real Madrid during Ancelotti’s two seasons in charge. When it really mattered, though, Real stepped up to the challenge.

The two Madrid sides met in the Champions League final in Lisbon six years ago. It was the first time the showpiece game had been contested by clubs from the same city, elevating the importance of the match to unprecedented levels. Ancelotti’s men rose to the occasion, triumphing 4-1 after extra time. The Italian will never face another derby that carries so much pressure. Compared to that game, tomorrow’s FA Cup tie will feel like a little local difficulty.

Yet beating Liverpool means a massive amount to Evertonians. The gulf between the clubs is huge and although Farhad Moshiri’s takeover four years ago provided an injection of cash and hope, the gap is growing. It is a decade since Everton tasted success in the derby and 21 years since they left Anfield victorious. Teams in two-club cities always measure their progress in relation to their neighbours, even when it is unrealistic to do so. Liverpool’s renewed ascendency at home and abroad makes Everton’s underachievement all the more painful. Derbies are the place where there is potential to claw back some dignity.

Klopp will not put out his strongest side. The FA Cup is low on the German’s list of priorities. This gives Ancelotti a chance to produce a result that will lift his team’s spirits. There is a strong belief at Goodison that, for the first time since Howard Kendall arrived in the early 1980s, Everton have a top-class manager. The downside of this is that the new man will be expected to produce positive traits on the pitch quickly. The rebuilding job on the blue side of Stanley Park will take time. The team lack balance, belief and pace. It would take a miracle for Ancelotti to compete with a full-strength Liverpool but the weakened side that Klopp is expected to deploy will raise ambitions that Everton can pull off a result. A disjointed performance in defeat would hurt morale. In that sense the cup draw has not been kind to the Italian. This first encounter on Merseyside has come too soon, before he can really impose his ethics on the side.

Anceotti defines himself by trophies. His new club have spent too long judging themselves against Liverpool. There is a sense at Anfield that the only time anyone thinks about Everton is when derby day rolls around. At Goodison they are obsessed with their local rivals.

This may not be a collision of equals and it carries nowhere near the significance of some of the derbies that Ancelotti has experienced but he will not underestimate the importance of the game. Everton’s primary ambition is to peg back Liverpool. That starts tomorrow. The man with the knack of winning derbies that really matter has a big job on his hands.