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Five of Jose Mourinho’s greatest managerial wins

Jose Mourinho has established himself as one of the greatest and most decorated managers of the 21st century, finding success in many of Europe’s biggest leagues and competitions.

Charismatic and occasionally controversial, there is no doubt that he has provided some memorable moments on and off the field. We’ve decided to look back at some of the matches which have defined his career.

Five of Jose Mourinho’s greatest managerial wins:

Manchester United 1-1 Porto (2-3 Aggregate) – 2003/04 UCL

After a league and UEFA Cup double in his first full season with Porto, Mourinho got his first shot at the biggest prize in European football. In the round of 16, Mourinho came up against Sir Alex Ferguson’s Manchester United, in what would be a precursor to their fierce Premier League rivalry.

After winning the first leg 2-1 at home, Porto headed to Old Trafford knowing that a draw would be enough to send them into the quarter-finals. After half an hour, Paul Scholes headed United ahead and the midfielder’s goal looked set to send the Red Devils through on away goals.

The game headed into injury-time with Mourinho and Porto on the brink of elimination, before Tim Howard failed to deal with a Benni McCarthy free kick and Costinha pounced to score a dramatic equaliser.

Cue Mourinho, who sprinted down the Old Trafford touchline in wild celebration, an enduring image which, along with his team’s success on the pitch, put him firmly on the footballing map.

Porto went on to win the Champions League with a 3-0 victory over AS Monaco in the final, making Mourinho the most sought after manager in Europe. It was Chelsea who eventually managed to secure his signature.

Chelsea 3-0 Manchester United – 2005/06 Premier League

Mourinho had taken the Premier League by storm in his first season to deliver Chelsea’s first title in 50 years, breaking a host of records in the process. The pressure was on to defend their title the following year, with Manchester United the only club to have previously won back-to-back championships in the Premier League era.

With three games to go, Manchester United headed to Stamford Bridge with Chelsea needing just a point to take the crown. What followed was an emphatic display as the Blues’ quality shone through to run out comfortable 3-0 winners, with an outstanding solo goal from Joe Cole the pick of the bunch.

It was the latest heavyweight bout between the league’s two foremost managers, with the self-proclaimed ‘Special One’ cementing his growing status as a great of the modern game. Sir Alex Ferguson conceded that, whilst he felt the result didn’t reflect his side’s performance, there was no doubting Chelsea and Mourinho were worthy champions.

Following the trophy presentation, Mourinho famously threw his winners’ medal into the crowd and after being given a replacement, promptly tossed that to the fans as well.

Bayern Munich 0-2 Inter Milan – UCL Final 2010

An honourable mention has to go to the semi-final second leg against Barcelona at the Camp Nou, where Inter – reduced to 10 men after Thiago Motta’s red card after just 28 minutes – lost 1-0 on the night but still progressed on aggregate. One of the truly great Mourinho masterclasses, Jose referred to the game as the “most beautiful defeat of [his] life.”

But it was the final against Bayern Munich at the Bernabeu which proved to be one of the crowning glories of his career. Having already secured the Serie A and Coppa Italia titles, Inter were aiming for a historic treble, with one of the greatest sides assembled in Italian football.

Mourinho’s side produced another typically resolute and clinical performance as they soaked up pressure from Bayern, who dominated the possession and attempts on goal. Inter stood firm and Diego Milito was able to capitalise on his opportunities, scoring twice to seal a 2-0 win and cap off a fine individual season for the Argentine.

In lifting the Champions League, Inter became the first Italian side to complete the treble. Mourinho became the third manager to do so in the Champions League era, cementing his status as a member of the European elite.

Noughties Nines: Diego Milito – Il Principe

Barcelona 1-2 Real Madrid – 2011/12 La Liga

Following his success in Italy, Mourinho took one of the most high profile and high pressure jobs in world football at Real Madrid, at a time when their famous rivalry with Barcelona was as fierce as it has ever been.

The Spanish giants had each assembled world class sides around the two best players in world football, Cristiano Ronaldo and Lionel Messi.

Despite amassing 92 points and scoring 102 goals in Mourinho’s first season at the helm, Madrid finished as runners up to their El Clásico rivals. The following year however, they found another gear.

Mourinho’s men headed to the Camp Nou in April 2012, just four points ahead of their rivals at the top of the table and with the title on the line. Sami Khedira gave the visitors the lead in the first half after Victor Valdes failed to deal with a corner, with the German scoring Madrid’s first goal on Barca soil since 2007.

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The hosts equalised in the second half though Alexis Sanchez, but just minutes later Ronaldo scored to give Madrid their first league victory over their old rivals for four years. In front of a silenced Camp Nou, Ronaldo famously celebrated with his ‘calma’ gesture to the home crowd.

After the game, Pep Guardiola conceded that the title race was over and the trophy would be heading to the Bernabeu. He was right, and Madrid topped the table with a record number of points (100) and goals (121). It was a huge achievement for Mourinho, overthrowing a side many considered to be one of the greatest in footballing history and doing so in such emphatic fashion.

Roma 1-0 Feyenoord – 2022 UECL final

Mourinho’s career after Real Madrid has been one of mixed fortunes, with another Premier League title on his return to Chelsea the obvious highlight. His tactics have been accused of being outdated and lacking the effectiveness of his early career, though he has still been able to find success.

In 2021 he returned to Italy, this time with AS Roma, and took the side to the Europa Conference League final in the competition’s maiden season. Once again, it was a typical Mourinho performance which ultimately saw Roma over the line.

Just as in the 2010 Champions League final, opponents Feyenoord had the lion’s share of possession and more attempts on goal. Roma dug in and defended valiantly, with Chris Smalling picking up the man of the match award, and clinched victory courtesy of Nicolo Zaniolo’s first-half goal.

The trophy was Roma’s first in 11 years and first-ever success in UEFA competition, leading to wild scenes of celebration in the Italian capital.

It was also a landmark moment for Mourinho, who won a European trophy with a fourth different club – a managerial record – and lifted his fifth continental prize in total. He also became the first coach to win all three European trophies, albeit in the first iteration of the Europa Conference League.

Despite success and trophies being harder to come by for Mourinho over the past decade, his victory with Roma was a reminder of his brilliance if it was ever needed. There is no doubting his place as one of the greatest managers of all time.

Read – Remembering Mourinho’s Inter side that beat Bayern in the 2010 UCL final

Read Also – Iconic Duos: Chelsea’s impregnable pairing made of steel and silk, Terry and Carvalho

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