An Andrea Belotti double at the Stadio Olimpico in Turin on last Thursday heaped more misery on both Marco Giampaolo as coach and AC Milan as a club in general, that was then compounded by an embarrassing defeat by Fiorentina at the Stadio San Siro just three days later.
When the Italian striker fired Torino level against the Rossoneri the fallout saw an outraged Pepe Reina sent off for his protestations, and Milan would do well to remember how far the Spaniard’s former club Liverpool fell back in the nineties.
On April 28, 1990 victory over Queens Park Rangers handed the Merseysiders the English championship for, what would be the final time, and ultimately end 20 years of dominance. A month later, Milan would defeat Benfica 1-0 in the European Cup final, during the early stages of resurrection as a major force in world football.
However, since securing the Serie A title back in 2010/11, the Rossoneri are trophyless – possibly harshly ignoring a 2016 Supercoppa di Italiana – and seem to be intent on making the same mistakes as their two-time Champions League final opponents.
While the resignation of manager Kenny Dalglish was difficult for Liverpool to stop, the appointment of former midfield general Graeme Souness is often cited as a significant reason behind the clubs fall from grace. Even if the ex-Sampdoria man did arrive with some coaching pedigree.
Like the Merseysiders, employing former players had been a huge success previously, with Fabio Capello and Carlo Ancelotti playing major roles in their revival. However, Clarence Seedorf and Filippo Inzaghi, who replaced title-winning Massimiliano Allegri, were virtually untested in top-level football.
In contrast, Milan had already begun casting aside those with plenty more to give, just as Souness had by offloading Peter Beardsley, Ray Houghton and Steve Staunton. Although few of those had the impact that Andrea Pirlo had on departing Milan – collecting another four Scudetti at Juventus.
Just as with outgoings, Liverpool started making multiple errors with their incomings. Paying eye watering sums for almost unheard of foreign imports (see Torben Piechnik) or attempting to shoehorn star players from clubs in the lower reaches of English football like Nigel Clough and Andy Carroll 20 years later.
Listing off the likes of M’Baye Niang, Andrea Poli, Carlos Bacca and Leo Duarte, will no doubt bring back painful memories to Milanisti minds of even more names they would label in the expensive failure category.
Whilst not entirely of their own doing, the Rossoneri continue to fall behind Juventus in commercial terms, as another proposed San Siro renovation or replacement is announced. Liverpool were their own worst enemy here, as they failed to simply hand over the money required to simply have Anfield expanded. A task that arguably came 20 years too late.
Sitting at the top of the Premier League, the Merseyside club may finally have rectified the mistakes of the past, although there have been false dawns before in 1996, 2001, but particularly the Champions League victory over Milan in 2005. That at least gives supporters something to cheer though.
This season, it will have been nine years since that last Scudetto and plenty of time has passed since there has appeared to be a single glimpse of light at the end of the tunnel, and it could well be 2040 before they are top of the Serie A standings if they do not get their house in order.