Milan will need to be at their best tonight to break their Spanish jinx and reach the Champions League quarter-finals as they cross swords with Atletico Madrid in the round of 16 first leg at the San Siro.
This will be the first encounter between Milan, seven-times European champions, and Atletico.
Milan have a poor record against Spanish clubs and only managed one win from their last eight encounters at home to La Liga opponents – a 2-0 first-leg success over Barcelona in February 2013.
In each of the last two seasons, Milan were dumped out of the competition by mighty Barcelona – in the quarter-finals in season 2011/12 and in the round of 16 last year.
Even worse, Milan were eli-minated from the Champions League in each of the last four ties against Spanish opponents in the knock-out stage – three times by Barcelona (2005/06, 2011/12 and 2012/13) and Deportivo La Coruna (2003/04).
For Milan, Clarence Seedorf will make his debut as coach in the competition he won with three different clubs as a player – Ajax (1994/95), Real Madrid (1997/98) and Milan (2002/03 and 2006/07).
Milan have a mammoth task to clear the Atletico hurdle.
The La Liga surprise package reached the last 16 as Group G winners, collecting 16 points in the process. They are one of only three teams to stay unbeaten in the group stage this season.
Milan, by contrast, had to sweat to make the runners-up spot theirs in Group H, four points behind leaders Barcelona.
In their last trip to Italy, Atletico Madrid beat Lazio 3-1 on their way to winning the 2011/12 Europa League.
In Spain, Diego Simeone’s side are currently engaged in a tight race with Clasico giants Barcelona and Real Madrid for the title, which could be their first since 1996.
Atletico, twice winners of the Europa League in the last four years, are vying for their first Champions League quarter-final appearance in 17 years, at a time when Simeone was a club player.
Although Atletico have experienced a slight dip in form in recent weeks, Milan enter tonight’s clash as underdogs.
Some critics, though, still reckon they have enough quality and experience within their ranks to eliminate the Rojiblancos from the competition.
However, whereas Atletico Madrid are very much involved in the race for league honours at home, the same cannot be said of Milan.
The Rossoneri never really took off this season so much so that a top-three finish is already beyond their reach.
Milan were also knocked out of the Coppa Italia quarter-finals by Udinese last month.
With hindsight, Milan must have committed a huge mistake in having started the season with Massimiliano Allegri still in charge of the team.
It was an open secret that the ex-Cagliari coach was never a favourite with club supremo Silvio Berlusconi and, at the end of this season, he would have left anyway.
Milan have shown better form with Seedorf around. But one still has to see whether the progress, no matter how big or small, is enough to see them through against Atletico.
With the 2013/14 campaign already past its halfway mark, Milan have two remaining objectives – making inroads in the Champions League or booking an Europa League berth by making a top-six finish.
Seedorf, meanwhile, has signed a long-term contract until June 2016. That means, the Dutchman will get enough time to build something of his own and prove himself.
The fans expect Seedorf to transmit enthusiasm and instil a winning mentality in his players starting from tonight’s clash while hoping that the glory days of the past return to the San Siro.