In a recent attempt to return to their former glory, significant investment has since been shot through the veins of the Rossoneri... without the desired effect.
The latest setback came in Milan's humiliating Europa League group exit at Olympiacos, stretching their last domestic or European title to eight years - as t
The Glory Years
In a two-way battle with Juventus, European dominance in Milan stretched across two decades between 1990 and 2010. T
In fact, they would become the first team in Italian top flight history to go an entire season unbeaten on their way to a 12th Scudetto in 1991/92, as their famous attacking philosophy and pivotal youth infrastructure began to take hold.
Trio Paolo Maldini, Franco Baresi and Demetrio Albertini twinkled under the floodlights of San Siro, in a spiral of home grown talent amidst an unprecedented trophy haul.
Although the turn of the millennium proved somewhat less endearing, the Rossoneri would then play home to two of their most influential players of all time. Among feared greats, including Andrea Pirlo, Filippo Inzaghi and Andrea Nesta, it was the names of Kaka and Andriy Shevchenko that proved integral.
Although they would play in Milan's famous Champions League final loss to Liverpool, Kaka would later help avenge their defeat to the Reds in 2006/07. However, no-one could have anticipated the plight of Italy’s most decorated force.
The Rossoneri would have to wait an agonising seven years for any means of success in 2010/11 – an 18th Serie A title triumph that was meant to re-ignite their renowned stature.
Instead, rivals Inter and Juventus would obliterate any hope of returning to former glory by winning 13 of the next 14 Serie A titles, as they wilted beyond the belief of their faithful following.
Lowly Finishes & Financial Mismanagement
A spate of disappointing domestic finishes, culminating in the sacking of six different coaches, left the daunting task of former Rossoneri Gennaro Gattuso - to turn around the club's fortunes in November 2017.
Meanwhile, substantial investment in excess of £200m under former Chinese owner Li Yonghong, including the acquisition of former Old Lady defender Leonardo Bonucci, would eventually see Milan return to European competition after a beleaguered four year absence.
Yet, their hopes of a first European triumph for over 10 years were dashed against Arsenal in the round of 16 stage, as Gattuso’s valiant attempt to galvanise the squad failed.
Whilst Bonucci returned to Juve after just one season, a
In a desperate attempt to rekindle the Rossoneri, US Hedge Fund Elliot Management took control of ownership in August 2018, overseeing eight new signings that included duo Gonzalo Higuain and Mattia Caldara.
The high profile signings looked positive on paper, yet none would have an impact as Caldara would suffer a long-term achilles injury, whilst Higuain's contribution would prove inept.
Despite finding themselves fourth in Serie A after 16 games, pressure to return to former European heights once again faltered.
Eliminated on the penultimate matchday by Olympiacos, the Greeks and Spain's Real Betis would pip Milan to last 32 qualification, leaving fans around the continent bewildered at yet another catalogue of failures.
So Where Do AC Milan Go From Here?
The Italian giants were hit with a one-year Europan ban last summer, after breaching FIFA's Financial Fair Play Regulations under Yonghong.
Likewise, on the field matters leave Gattuso scrambling for answers, as it remains increasingly unclear as to the timing of Milan’s next trophy in a quite frankly, horrendous era.