Italy will lose one of its four Champions League spots next season, as Germany's Bundesliga claimed an extra place based on UEFA rankings, but AC Milan and Napoli were handed the opportunity Friday to boost Serie A.
AC Milan and Napoli both finished second in their groups, behind two favorites for the Champions League title, Barcelona and Bayern Munich, respectively. And the draw put the Italians against the remaining English clubs in the last 16.
Milan will play Arsenal in the first knockout stage, and Napoli plays Chelsea. Add in the fact 2010 European champion Inter Milan also advanced, giving Serie A the most clubs of any league in the last 16, and the trio could shake up the tournament this season.
Although eliminating Arsenal and Chelsea would not reclaim the lost berth, it would be impressive if Serie A places three clubs in the quarterfinals, and at the expense of England having none.
With both Manchester City and Manchester United eliminated at the group stage, England's Champions League season could be over early next year. For Italy, it would mean putting multiple squads in the final eight for the first time since 2006-07, and three for the first time since 2005-06.
Although AC Milan (2007) and Inter (2010) have won European titles, the league has otherwise struggled on the world's biggest club stage. That is a huge part of why Serie A lost one of its CL spots, and a part of the reason that Milan and Napoli need to break the recent jinx.
For the record, Germany has not fared much better in the Champions League over recent years, as it has not placed two clubs in the quarterfinals in the same season since the knockout stage was expanded to 16 teams.
However, Germany's teams have accumulated more points in Europe, including the Europa League, to claim the spot at the expense of Italy.
Although the Italians are outsiders to claim the championship this year, if all three make the last eight, Serie A would take a major step toward reclaiming some luster off a recent string of poor performances in the Champions League.
Easier said than done, of course, as it is possible all three exit in the last 16, and leave Serie A's hopes of reclaiming the lost berth a distant dream.
Bayern Munich vs. Basel
Basel slayed Goliath in the group stage, eliminating Manchester United with a surprise 2-1 win on the final matchday, but do not expect another miracle from David at this stage. Only Barcelona and Real Madrid trump Bayern's talent, and with the final in Munich, this series should actually provide a rest after the German giants conquered the "Group of Death."
Winner: Bayern Munich
Inter Milan vs. Marseille
Inter Milan was in poor form early this season in Serie A, but it has won four of its last five to surge into the top half of the league. And in Europe, it had no problem, as it cruised to first place in its group. If Wesley Sneijder is healthy early next year, Inter will be dangerous. Marseille has also been a Jekyll and Hyde club with its domestic form weak, but this matchup in Europe will be tough.
Winner: Inter Milan
Benfica vs. Zenit
Benfica is back in the knockout stage for the first time since 2005-06, when a win over reigning European champion Liverpool in the last 16 helped it advance to the quarterfinals. Playing a Russian side at this stage is not an easy job, but if Benfica is going to make the most of this knockout appearance, the draw could not have gone much better.
Real Madrid vs. CSKA Moscow
Real Madrid ended its run of last 16 exits last season and CSKA Moscow will be nothing more than a speed bump for Jose Mourinho's club at this stage. Playing in Russia will be no easy task, but Real Madrid - despite its recent defeat to Barcelona - is still the team with the best shot to dethrone its Spanish rival in the Champions League.
Winner: Real Madrid
Chelsea vs. Napoli
Napoli became one of the rare pot 4 teams to escape group play (APOEL also did this year), and could be one of the most underrated sides in the final 16. The Italian side could have benefited from an easier draw, but after besting City in group play, another English side could also have trouble with the Italians. The winner of this matchup will be dark horse the rest of the way.
Arsenal vs. AC Milan
Easily the best matchup of the first knockout round, this one truly is a toss- up. Arsenal, despite the loss of Cesc Fabregas and Samir Nasri, has regained a bit of its old, strong form, and can never be overlooked at any stage. Milan's a team that doesn't scare anybody at this stage, but a team that will compete. Robin van Persie will be the difference in this series.
APOEL vs. Lyon
APOEL became the first club from Cyprus to reach the knockout stage, and with the draw against Lyon, further advancement is possible. Once again, the Cyprus side will be the underdog, but Lyon would be foolish to underestimate the team nobody gave a chance to escape group play. APOEL has the chance to make a name for itself here, but neither side will survive in the next round.
Barcelona vs. Bayer Leverkusen
All Barcelona does is win, and Bayer Leverkusen will not be able to solve the European champions at this stage either. Leverkusen could have sneaked through with just about any other draw, but even without David Villa - who suffered a broken leg this week in the Club World Cup - Barca remains the most complete and dangerous club in Europe.