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A look at whether the Serie A side’s run will continue in the future

COMMENT
By Adam Scime

AC Milan's Champions League campaign ended early on Wednesday night, as they bowed out at White Hart Lane in a case of 'so close, yet so far away' with William Gallas clearing Robinho's strike off the line.

Since winning the competition in Athens in 2007, AC Milan have been unable to come close to repeating that feat - a trend reminiscent of Real Madrid's 'last 16' malaise in Europe's top competition.

A Carlo Ancelotti-coached and Kaka-inspired side were the dominant force in Europe in the mid-section of the noughties. Always a pleasure to watch, the Serie A outfit were a team that had both imagination and a conqueror's resolve - winning in 2003 on penalties against Juventus, narrowly losing the final to Liverpool in 2005, being edged by Barcelona in the semi-finals in 2006, and finally gaining revenge on the Reds in 2007 by lifting the Cup courtesy of Filippo Inzaghi's brace.

RECORD IN EUROPE | Real Madrid v AC Milan
Year
2001-02
2002-03
2003-04
2004-05
2005-06
2006-07
2007-08
2008-09
2009-10
2010-11
Real  Madrid
Winners (CL)
Semis (CL)
Quarters (CL)
Last 16 (CL)
Last 16 (CL)
Last 16 (CL)
Last 16 (CL)
Last 16 (CL)
Last 16 (CL)
?????
AC Milan
Semis (Uefa Cup)
Winners (CL)
Quarters (CL)
Final (CL)
Semis (CL)
Winners (CL)
Last 16 (CL)
Last 32 (Uefa Cup)
Last 16 (CL)
Last 16 (CL)
The Italians' latest humbling against Tottenham is the third time in the last four seasons they have been eliminated in the 'Sweet 16' stage of the Champions League and all three times by English opposition.

Arsenal shocked AC Milan at the San Siro in 2008, while Wayne Rooney and Manchester United absolutely demolished Leonardo's men 7-2 on aggregate in 2010. In between, they were undone by Werder Bremen in the Round of 32 of the now defunct Uefa Cup.

A disturbing trend of underachievement is emerging that bares resemblance to a once glorious Real Madrid side that slipped into continental mediocrity.

Madrid, with star names Raul, Fernando Hierro, Roberto Carlos, Zinedine Zidane and Luis Figo among others, won three Champions League trophies from 1998 to 2002 in a richly successful era for the Spanish powerhouse, possessing a squad that was a clear favourite to win every campaign. However, they have not come close to earning that elusive 10th European crown for that last six seasons, enduring elimination from the Round of 16 in their last half-dozen attempts to Juventus, Arsenal, Bayern Munich, Roma, Liverpool and Lyon.

AC Milan were never capable of winning this season's Champions League, but have they developed a 'curse' of their own that will rival Real Madrid's? The results say they are on their way there.

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