Manchester United may not have produced the most exciting display in the 1-0 win over Galatasaray on Wednesday night, but the result marked a landmark moment for Sir Alex Ferguson.
The Scot became the first manager to record a century of wins in the Champions League in his 18th consecutive season in Europe's elite competition.
It is a quite remarkable achievement for a manager who is as passionate about the game now, as he was when he took up his first managerial role at East Sterling some 38 years ago.
Ferguson has watched on with both despair and delight as he looks to cement his legacy in the history books by winning the European Cup on three occasions. Liverpool's Bill Paisley is currently the only man to achieve this feat and and the 70-year-old would dearly love to match this record before walking away from the game.
As Ferguson goes in search of a record-equalling third title, we have decided to pick the five Champions League games which have helped define this sensational era.
Manchester United 3-2 Juventus, 1 October 1997
This may have just been a group game but it signified a momentous occasion for Sir Alex. Facing the previous seasons defeated finalists just one year after being soundly beaten both home and away by the La Vecchia Signora, United wanted to make a statement.
With summer signing Teddy Sheringham making his debut in the competition, there was an electric atmosphere at Old Trafford as United looked to turn their domestic dominance into silverware in Europe. Goals from Sheringham, Paul Scholes, and a sensation solo effort from Ryan Giggs handed Ferguson a satisfying victory. It was a glimpse of what this side was capable of doing and a precursor to further success.
Manchester United 2-1 Bayern Munich, 26 May 1999
Where do you start with this game? United were missing the suspended duo of Roy Keane and Paul Scholes, found themselves trailing after just six minutes thank to a free-kick from Mario Basle, and after ninety minutes were still 1-0 down.
Then came three of the most incredible minutes in United's history. Ferguson had earlier gambled and made the decision to bring on two strikers in Teddy Sheringham and Ole Gunnar Solskjær. Both would find the net as Bayern failed to deal with corners from David Beckham and the most dramatic comeback in European history was complete. As the United players celebrated wildly with their manager, the Bayern players were left shell shocked, barely able to move and comprehend what had happened. Ferguson had finally got his hands on the European Cup.
Benfica 2-1 Manchester United, 7 December 2005
A United side containing Scholes, Giggs, Ferdinand, Ronaldo, Rooney and Van Nistelrroy simply needed to secure a draw in order to scrape out of the group stages of the competition. Against an injury ravaged Benfica side, no-one would have predicted a problem - the last time United had failed to make it out of the group stages was in the 1995/96 season.
Having taken the lead through Scholes, Benfica responded and goals from Geovanni and Beto handed them a win which condemned United to fourth place in a group which also contained Villarreal and Lille. It was a campaign, and performance, which Ferguson would rather forget, but it forced him to look at his squad and the following season United made it to the semi-finals were they were beaten by an inspired AC Milan side.
Manchester United 1-1 Chelsea [6-5 on penalties], May 21 2008
The first all-English final in the history of the competition and an important year for Manchester United as a club. It had been 50 years since the Munich air disaster and Ferguson was hoping to pay a fitting tribute to the players that lost their lives by delivering another European Cup.
Goals in the first half from Cristiano Ronaldo and Frank Lampard meant that there was nothing to separate the two sides. In the second half Didier Drogba hit the post, while in extra-time the striker became just the second man to be sent off in a final. This time there was no late dramatic winner in injury time. The drama would come during the penalty shoot-out. Out of the first nine penalties only Ronaldo had missed. John terry stepped up to win the trophy for Chelsea, only to slip over and see his shot cannon off the post. Anderson, Giggs and Kalou all scored, before Nicolas Anelka's penalty was saved by Man of the Match Edin van der Saar.
Barcelona 3-1 Manchester United, 28 May 2011
Two years prior to this game, Barcelona had denied Ferguson a third Champions League trophy as Samuel Eto'o and Lionel Messi provided the goals in a one-sided contest. This was to be United's chance at revenge, an opportunity for the Scot to draw level with Paisley. It was the power of United against the Tiki-Taka football of Barca.
In the first half Barcelona had 22 shots on goal and enjoyed a staggering 58% possession, yet the scores were level thanks to Rooney cancelling out an effort from Pedro. In the second-half, Pep Guardiola's side put on a football clinic. Goals from Messi and David Villa secured a 3-1 win and United had once again fallen to the might of Barcelona.
But there was no time for regret and Ferguson is once again looking to win the Champions League in his 18th season in the competition. With 100 wins already under his belt, there is little doubt that he is one of the greatest managers ever to grace the European Cup.
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