The 2013/14 season offered little satisfactions to Milan who ended the campaign a disappointing eighth in the Serie A, a massive 45 points behind champions Juventus and trailing less-quoted sides such as Parma and Torino.
Throughout the campaign, the Rossoneri were never in contention for a top-three finish and it was only in the closing weeks of the season that they mounted a decent challenge for a place in Europe.
But that was not enough for Milan who are facing the stark reality of missing out on European football for the first time since 1999.
Last season, Milan were ousted from the Champions League by Atletico Madrid in the first knock-out stages whereas modest Udinese were their executioners in the Coppa Italia.
All in all it was a poor campaign for Milan, who even resorted to the change of coach midway through the season as Clarence Seedorf replaced Massimiliano Allegri.
Milan improved considerably with Seedorf. The team collected 22 points in their 19 first-round outings under Allegri but once the Dutchman took charge they amassed a remarkable 35.
Still that was not enough for Seedorf to keep his job as he is likely to be replaced by youth team coach Filippo Inzaghi.
Seedorf was still under contract with Milan until 2016 and his sacking is set to cost the club millions of euros, another administrative blunder that blighted the club these past few years.
It is difficult to understand why the Rossoneri had handed Seedorf a two-and-a-half year contract only to show him the backdoor just six months later.
That was not the first of a series of bad decisions taken by the Milan hierarchy as this time last year they opted to retain a clearly demotivated coach in Allegri, who did not enjoy the confidence of supremo Silvio Berlusconi.
Milan also erred badly when it came to transfer dealings.
One questions why did Milan refuse a €15m offer from Chelsea for Andrea Pirlo in the summer of 2009, only to let him leave for free two years later and join rivals Juventus?
In the last three years, Pirlo’s class was decisive to shift the balance of power from Milan to Turin.
In January 2012, Milan also turned down a very favourable Paris SG offer, touted to be in the region of €28m, for Alexandre Pato.
A year later, Milan were left to rue their stance as they offloaded the injury prone Pato to Corinthians for a cut price of €15m.
Moreover, had Pato signed for PSG in January 2012, the move would have given Milan the opportunity to land then unsettled Manchester City striker Carlos Tevez. The Argentine eventually signed for Juventus at a bargain price of €10m.
Realistic targets
Milan need a business approach to turn around their fortunes.
They have not been European champions since 2007 and the last time they won the Serie A title was in 2011.
It will take some time before Milan will become a force to reckon with unless Berlusconi starts investing heavily in the club or opts to sell to an investor who has the financial muscle and desire to see the Rossoneri becoming competitive in the near future.
In the short term, the club should set realistic targets, stop signing seasoned players and instead give up-and-coming players a chance to prove themselves.
Above all, Milan should stop living in denial and admit the club is in a phase of transition, unable to compete for the major honours.
The best way is to set medium to long-term objectives and patiently start assembling another formidable side. Under normal circumstances, that could take between three and five years to happen.