Los Blancos head into Saturday's derby against Diego Simeone's side in third place with their Liga hopes dashed in what is fast turning into yet another forgettable campaign
Ancelotti's side finished in third place in the Italian's first campaign at the Santiago Bernabeu as Atletico claimed the title, although that campaign was saved spectacularly by winning the Champions League and the Copa del Rey. This term, however, such a happy ending seems highly unlikely.
The Copa del Rey is already gone. Madrid were eliminated from the cup competition for fielding the ineligible Denis Cheryshev against Cadiz in December and failed in an appeal to overturn that decision. Then, in early January, Benitez was sacked after a 2-2 draw at Valencia and replaced by Zinedine Zidane.
The Madrid media spoke of a 'Zidane effect', but if such a thing did ever exist, it has already worn off. Away from home in La Liga, Real have won only one of the Frenchman's first three games and the two dropped points at Malaga on Sunday mean the Primera Division is now almost certainly heading back to Barcelona for a sixth time in eight seasons.
That is Madrid's worst run in La Liga since the days prior to the arrival of Alfredo Di Stefano in 1953. Before the Argentine attacker joined to lead the club to their most glorious era in the late 1950s and early 1960s, Real went 17 seasons without winning the Primera Division.
That means the current streak is the second-worst in the Blancos' entire history and it is not good enough, especially because Madrid are the world's richest club. Back in the early 1980s, Real were broke and often forced to sell their best players. But not now.
Figures from Deloitte have placed Madrid at the top of the list of football teams with the highest incomes for the past three years, with total earnings in excess of €500 million. Yet it has counted for little in terms of titles - at least since the club claimed La Decima in 2013-14.
Real brought in €577m to be precise according to this year's figures, three times the total income accrued by Atletico (€187m), with the Rojiblancos third in Spain but 14th overall on the list of Europe's richest clubs.
Asked about the budget difference of almost €400m between the two teams, Simeone said on Friday: "The economic differences are real. In the long run, the one with the bigger budget usually finishes higher because they have more alternatives. That's the logic."
With 25 games played, however, Atleti are ahead of Real and there is no guarantee that will change before the end of the season - especially with Madrid struggling away from home and still to face Barcelona at Camp Nou in April.
In the derby, meanwhile, Madrid have won only one of the last nine meetings with their city rivals. That came in the Champions League quarter-final second leg at the Bernabeu last season - a last-gasp 1-0 thanks to a Javier Hernandez strike after Arda Turan had been sent off and the Rojiblancos reduced to 10 men.
So what would it mean for Atleti to finish second in La Liga this time around? "It would be a continuation of our work over the past six months," Simeone said. "Coming second is always better than coming third."
Indeed it is and Madrid will no doubt feel the same. Second is not really seen to be sufficent for Real, so third place below their two main rivals really would be a big blow for the Blancos in an already calamitous campaign.
"It is a derby, but it is just another game," Zidane said on Friday ahead of his first fixture against Atletico as coach. "We have to give our maximum as always and continue with our idea of playing. We know it is going to be difficult, that is clear."
Recent results certainly suggest that will be the case, but the Frenchman added: "It will always be difficult if we drop points, but we have games left and we have the Champions League, so we are concentrated on our work and whatever happens, our season won't end tomorrow."
That is true, but the Champions League will be anything but easy and if Madrid fail to overtake their city rivals in the run-in, it will be a disappointing start for the 43-year-old coach.
La Liga is virtually impossible now and that is not entirely his fault, but finishing below both Barca and Atletico would represent yet another embarrassment in a season of debacles for Los Blancos.