2008-2009 (The Year With No Champions League)

After a poor domestic season that finally resulted in Milan missing out on the Champions League, the club made numerous additions during the offseason signing Ronaldinho, Andriy Shevchenko, Gianluca Zambrotta, Marco Borriello and Mathieu Flamini, amongst others. They also added international sensation David Beckam during the January transfer window on loan from MLS's LA Galaxy. The season started poorly with two consecutive losses. However the team bounced back, rising to third place in the table at the midway point of the season, six points shy of leaders F.C. Internazionale Milano.

With Milan's failure to qualify for the 2008-09 edition of the Champions League, the team has had some success in the 2008-09 UEFA Cup, winning their group and advancing to the knockout stage.

2007-2008 (5th in Serie A, Eliminated First Knockout Round in Europe, Won FIFA Club World Cup)

Hot off the heels of winning their seventh Champions League title, Milan continued their international success by winning the 2007 UEFA Super Cup against Sevilla FC in a game marked with sadness over the recent on-field death of Sevilla player Antonio Puerta. Milan's Champions League success also made the club eligible to compete in the 2007 FIFA Club World Cup where they would win their 18th officially recognized international trophy - tied for most club international trophies in the world. Ironically, Milan won their 18th title in a match against Boca Juniors, the team they are tied with in total international trophies.

However, these two trophies only served as consolation for a very disappointing season for Milan. The club had a slow start in Serie A, often finding it difficult to score after a pre-season injury to Ronaldo. This coupled with their aging backline and some deteriorating performances by Dida, found the club in mid table for much of the season. New signing Alexandre Pato was a bright light for an otherwise dark season for Milan. By the end of the Serie A campaign, AC Fiorentina edged Milan out for fourth place in the standings and thus Milan failed to qualify for the 2008-09 Champions League - their first failure since the 2001-02 season.

Milan's involvement in the 2007-08 edition of the UEFA Champions League was also forgettable. While the club won its group, they were quickly eliminated by a much younger opponent, Arsenal FC in the first knockout round. Prior to this season, Milan had made it to at least the quarterfinals of every Champions League going back to the 2002-03 edition.

2006-2007 (4th in Serie A, Won UEFA Champions League)

Milan's Serie A campaign began with the aforementioned -8 points penalty resulting from the Caliopoli Scandal. After a lackluster first half of the season which saw Milan hover at the center of the standings, several January transfers (including World Cup member Massimo Oddo, and Brazilian legend Ronaldo) reinvigorated the club. By the end of the campaign, Milan surged up the table to finish fourth, thus assuring their participation for the 2007-08 UEFA Champions League.

While their Serie A campaign proved moderately successful, the 2006-2007 season is best remembered for the team's performance in the Champion's League. The penalties imposed after the Calciopoli scandal resulted in Milan being seeded third in the final 2005-06 Serie A table. Thus the team was forced to play in the Champion's League Qualifers against former European champion Red Star Belgrade. Milan were victorius in the qualifier and advanced to the group phase which they would eventually win.

A.C. Milan starting lineup against Liverpool F.C. in Athens.

Milan survived a first round fight, defeating Celtic (eventual champions of the Scottish League) 1-0 on aggregate after an extra time goal by Kaká. Milan would go on to defeat European giant FC Bayern Munchen 4-2 on aggregate (2-2 at San Siro and 2-0 at Allianz Arena).

With the win over Bayern, Milan was propelled to the Champions League semi-finals. This marked the third consecutive and fourth time in five years that AC Milan has reached the final four of the competition. The first leg of the semi-final was played against Manchester United at Old Trafford. Manchester scored early on a goal from Cristiano Ronaldo, but Milan answered back thanks to a brace from Kaká, taking a 1-2 lead at half time. Manchester United would ultimately prove victorious thanks to two 2nd half goals from striker Wayne Rooney. This match was regarded by the media and UEFA President Michel Platini as the greatest match in recent memories.^{[citation needed]} The second leg of the Semi Final was played at San Siro on 2 May. Milan played a near perfect first half taking a 2-0 lead into halftime with goals from Kaká and Clarence Seedorf. A 78-minute goal by Alberto Gilardino sealed the victory for the home side.

Milan advanced to the UEFA Champions League final, pitting them in a rematch against their 2005 finals opponent Liverpool FC. The match was played at the Olympic Stadium in Athens, Greece, on 23 May 2007, with Milan prevailing 2-1 with both goals coming from Filippo Inzaghi. With the victory, the club affirmed its status as one of the powerhouses of European football, with three European Cup final appearances in five years, including two victories.

2005-2006 (3rd in Serie A, Semi Finals in European Cup)

Milan's Serie A campaign appeared to be one of their most successful in recent years. The team ended the season with a league high 28 wins, but could not edge Juventus in the standings thanks to their (at the time) record setting pace of 91 points. However all this success was nullified by the Calciopoli scandal. Milan were named in the Serie A scandal of 2006 and deprived of 44 out of the 88 points they gained in Serie A 2005-06. In addition, Milan would start their 2006-07 campaign with minus 15 points. Later, however, these point deductions were reduced, to 30 and minus 8 respectively, giving Milan the chance to compete in UEFA Champions League 2006-07.

Milan's efforts in the Champions League that year also proved close, but ultimately unsuccessful. After coming out on top of their group, Milan advanced to the knockout phase of the UEFA Champions League 2005–06, first defeating FC Bayern Munich of Germany on aggregate and then Olympique Lyonnais 3-1 on aggregate. Advancing to the semi-finals of the competition, they were defeated by eventual champion FC Barcelona of Spain 0-1 on aggregate, thus ending their Champion's League run for that season

2004-2005 (2nd in Serie A, 2nd in European Cup)

Hernán Crespo proved to be a solid signing. Massimo Ambrosini scored an incredible late goal against PSV Eindhoven. However, the season ended in disastrous defeat in Istanbul's Atatürk Stadium. In 2005, Milan let a 3-0 half time lead in their Champions League Final against Liverpool F.C. of England slip to a 3-3 draw. They conceded 3 second half goals in a span of 6 minutes, before losing on penalties. The nightmare of La Coruna was now replaced with a new nightmare of Istanbul. Milan ended the season being 2nd in the League and won the Italian Super Cup, defeating Lazio. 2004-2005 could be summed up as another solid season, but Liverpool won the European Cup and Juventus was the champion of Italy.

2003-2004 (Champions in Serie-A, Quarter Finals in European Cup)

Milan set a points record to win the scuddetto with a team that is largely still in place today. An attack spearheaded by Shevchenko, playmaking by Kaká, and defence with Nesta and Maldini. Milan's season was not perfect as they were beaten by Deportivo La Coruna 0-4 in the quarter finals of the European Cup after winning 4-1 in the San Siro. Despite being Italian champions, Milan showed, as some critics said, weak midfield character that would repeat itself in the European Cup final in the following season. Nevertheless, the squad proved successful and able to express a brilliant style of play for many months.

Right at the top: Ancelotti years

2002-2003 (3rd in Serie A, Champions of European Cup)

AC Milan ended the season with their sixth Champions League trophy in 2003. On route to the final in Manchester, England, Milan beat their cross city rivals Internazionale in the semi-finals and they ended the competition on a glorious note by beating their other Italian rival, Juventus, in a dramatic penalty shoot-out. That same season, Milan placed third in Serie-A. They also won the Coppa Italia and European Super Cup. Champions League winning starting line-up was: Nelson Dida; Alessandro Costacurta, Alessandro Nesta, Paolo Maldini, Kakha Kaladze; Gennaro Gattuso, Andrea Pirlo, Clarence Seedorf; Manuel Rui Costa; Andriy Shevchenko, Filippo Inzaghi. Then the following season, Milan signed Kaká. The team earned the nickname I Meravigliosi (The Amazing's).