The Most Surprising Champions League (UCL) Winners of all Time

As one of the most coveted prizes in club football, the UEFA Champions League has been dominated by a select number of teams - But there have been underdog wins and shocks in the UCL...

Since launching as the European Cup in 1955, 22 clubs have lifted the iconic silverware. Success in the UEFA Champions League can make or break a club’s season, creating stars and outstanding managers.

While the likes of Real Madrid, AC Milan, Liverpool, Barcelona, Ajax, and Bayern Munich have won the Champions League several times, there have been teams that have surprised football fans by unpredictably being crowned European champions.

José Mourinho Winner
Portuguese coach José Mourinho has been involved in two surprising Champions League wins, with the first being with Porto in 2004.

Porto (2003-2004)

Although Porto had a longstanding history of being one of three clubs to dominate Portuguese football, they had little success on the continent since their first European Cup win in 1987. Nevertheless, led by charismatic coach José Mourinho, FC Porto entered the 2003-2004 UEFA Champions League as underdogs, despite being the current UEFA Cup (now known as the UEFA Europa League) holders.

After finishing second in their group behind Real Madrid, Porto faced a difficult Round of 16 knockout tie against Manchester United. However, two goals from Benni McCarthy in the first leg at the Estádio do Dragão made sure the Portuguese side eventually went through on a 3-2 aggregate win. Next up was French Ligue 1 Champions Lyon. Again, a home win with goals from Deco and Ricardo Carvalho assured Porto would go through to the Semi-Final. Here they faced the equally unfancied Deportivo La Coruña of Spain. After a 0-0 draw at home, the second leg was decided by a 60th-minute penalty from Derlei sending Porto through to their second European Cup final.

Held at the Arena AufSchalke in Gelsenkirchen, Germany, Porto once again aced French opposition in the form of AS Monaco. Both teams were considered underdogs, as Monaco had knocked out Real Madrid and Chelsea in their route to the final. Yet on the night, it was Porto who would come out victorious. Goals from Carlos Alberto, Deco and Dmitri Alenichev gave Mourinho’s side a 3-0 win.

Porto’s 2003-2004 Champions League achievement made the top clubs take notice and Mourinho joined Chelsea just days after the final, taking defenders Carvalho and Paulo Ferreira with him. While Deco moved to Barcelona.

Liverpool Champions League Celebration
Liverpool fans celebrated their memorable Champions League victory after a surprising win in Istanbul.

Liverpool (2004 – 2005)

Even though Liverpool had achieved plenty of success in the European Cup with four titles, they hadn’t won the cup for over 20 years. The Merseyside club scrapped into the Champions League having finished 4th in the English Premier League the season previously, meaning they would have to qualify for the Group Stage. Having overcome Austria’s Grazer AK 2-1 on aggregate, they would be placed in a group alongside AS Monaco, Deportivo La Coruña, and Olympiacos of Greece.

With mixed results in their first five games, Liverpool needed to beat Olympiacos at Anfield to qualify for the knockout stages. Thankfully goals from Neil Mellow and Steven Gerrard created a memorable European night on Merseyside.

The Round of 16 saw Liverpool defeat Bayer Leverkusen twice with goals from Luis Garcia proving to be vital. Against Juventus in the Quarter-Finals, Garcia contributed again with Sami Hyypiä also scoring to give them a 2-1 advantage as they headed to Turin for the second leg. Here, they played a 0-0 draw, meaning they would face favourites and fellow English side, Chelsea, in the Semi-Finals.

After a tricky 0-0 first-leg draw at Stamford Bridge, Garcia’s controversial fourth-minute “ghost goal” gave Liverpool the lead and eventual win to send them to the final in Istanbul. The 2005 Champions League Final between Liverpool and AC Milan is a classic. The Italian side scored in the first minute thanks to veteran defender Paolo Maldini, before two goals from Hernan Crespo gave them a 3-0 lead before half-time. Rafa Benitez’s Liverpool side faced an almost impossible task in the second half.

Nevertheless, a change to a  3–4–2–1 formation with Dietmar Hamann replacing Steve Finnan would be the start of a miraculous recovery. Captain Steven Gerrard scored in the 54th minute before Vladimír Šmicer reduced the deficit to 3-2 just two minutes later. Spaniard Xabi Alonso completed the fight back on 61 minutes to make it 3-3, sending the game to extra time. Both sides had a few chances in the extra time, with Liverpool suffering fatigue.

A dramatic penalty shoot-out saw Liverpool goalkeeper Jerzy Dudek be the hero on the night. After saving Milan’s first two penalties, before Jon Dahl Tomasson and Kaká scored theirs. While Hamann, Djibril Cissé, and Šmicer gave Liverpool a 3-2 advantage. Milan’s star striker, Andriy Shevchenko, stepped up to take their fifth and final penalty. Dudek sealed Liverpool’s surprise victory with a left-hand save.

Diego Milito Champions League
Inter Milan’s Diego Milito scored two goals against Bayern Munich to give the Italian side a Champions League title in 2010.

Inter Milan (2009-2010)

Although Inter Milan had a presence in the Champions League for several years, they hadn’t lifted the European Cup since 1965. While they had plenty of domestic success with four back-to-back Serie A league titles, the “Nerazzurri” were still unfancied on the European stage. This is despite the leadership of José Mourinho and new arrival Samuel Eto’o upfront. Placed in a so-called “group of death” alongside Barcelona, Dynamo Kyiv of Ukraine and Russia’s Rubin Kazan, and despite drawing their first three games, Inter finished second in the group.

In the Round of 16 of the knockout stages, Mourinho faced his former Chelsea side, winning both ties to give the Italian side a 3-1 win on aggregate. While two 1-0 wins against CSKA Moscow saw them go through to the Semi-Finals where they once again faced Barcelona. Pep Guardiola’s side was the current Champions League holders, and considered favourites to retain the title. However, goals from Diego Milito, Wesley Sneijder, and Maicon gave Inter a 3-1 win at the San Siro in Milan. The second leg saw a resistant Inter survive Barcá’s attacking threat with only a Gerald Piqué game giving the Spanish side a 1-0 win on the night. However, it wasn’t enough as Inter went through to the final.

Inter would come up against another European giant, Bayern Munich, in the final. Held at the Santiago Bernabéu in Madrid, Spain, Diego Milito would grab the headlines with two goals to give Inter a 2-0 win to complete a treble-winning season, adding to their Serie A and Coppa Italia titles.

Like after his Champions League victory with Porto, Mourinho would leave Inter for Real Madrid in the summer of 2010. While Inter hasn’t come close to tasting European success since.

Chelsea Surprise Winners
Chelsea surprised many with their first Champions League victory in 2012.

Chelsea (2011-2012)

Since being takeover by Russian oligarch Roman Abramovich in 2003, Chelsea had become one of England’s most successful clubs, especially under the leadership of José Mourinho, and later Carlo Ancelotti. Yet the arrival of Andre-Vilas Boas in 2011 didn’t work out as he was sacked in March 2012. With former player Roberto Di Matteo coming in as caretaker manager, he would help the London-based club to their first Champions League trophy.

10 days after his arrival, Di Matteo overturned a 3-1 first-leg defeat against Italy’s Napoli side to eventually win 5-4 on aggregate after extra time at Stamford Bridge. The Quarter-Finals saw Chelsea beat Benfica of Portugal twice for a 3-1 aggregate win. However, the Semi-Finals wouldn’t be so easy facing a difficult test against Barcelona. While a 1-0 home win gave Chelsea an advantage as they headed to Camp Nou, the second leg was a dramatic affair. Captain John Terry was sent off in the first half for violent conduct, while goals from Sergio Busquets and Andreas Iniesta gave Barca a 2-1 lead on the night (Ramires gave Chelsea a late first-half goal). With the game heading to extra time in the dying minutes, a resistant Chelsea countered with Fernando Torres scoring to give them a 3-2 aggregate win.

The final was equally dramatic. Facing Bayern Munich at their Allianz Arena home stadium. Thomas Müller gave the German side a lead in the 83rd minute before Didier Drogba equalised just five minutes later to take the game to extra time. The two sides couldn’t be separated as the Final went to penalties. With Chelsea having suffered penalty heartache against Manchester United in Moscow in 2008, they wouldn’t go through it again. David Luiz, Frank Lampard and Ashley Cole converted their penalties for Chelsea, as did Philipp Lahm, Mario Gomez and goalkeeper Manuel Neuer for Bayern. However, Petr Cech would save Ivica Olic and Bastian Schweinsteiger’s attempts before Drogba slotted home the winning penalty for Chelsea.

In 2021, another mid-season managerial change once again led to Chelsea winning the Champions League under manager Thomas Tuchel.

This season (2022/23) Chelsea have sacked Tuchel. Could they repeat the hat trick of mid season sackings, leading to a surprising Champions league win? The odds are against them at 14/1, according to this online football betting site.

Why the Champions League delivers

Despite the usual suspects often being involved in the latter stages, the Champions League has produced some classic underdog stories with relative minnows winning and teams struggling domestically ending the season as UCL champions. As we have seen in the FIFA World Cup, the structure group followed by knockout games lends itself to shocks and surprises. To many it is the best club football competition in the world and the history of The Club World Cup winners suggests its the highest quality.