The year 2007 marked something of a changing in the guard in terms of football’s biggest names.
In 2006, Cristiano Ronaldo and Lionel Messi were simply promising young talents on the rise.
But in the space of 12 months they became superstars on the cusp of the Ballon d’Or.
After taking some time to find his feet in English football, Ronaldo had been dominant, forming a breathtaking on-field relationship with Wayne Rooney after the controversy of the 2006 World Cup.
By April, Ronaldo was spearheading a Premier League title charge and United’s Champions League dreams were well and truly alive.
He scored twice in a 7-1 thrashing of Roma in the Champions League quarter-finals at Old Trafford, a prime example of Ferguson’s side at their swashbuckling best.
Just one team stood between United and an all-English final against either Liverpool or Chelsea - AC Milan.
And whilst Ronaldo was inspiring United to great things, Carlo Ancelotti’s experienced side were leaning on the magic of Kaka.
It took Ronaldo just five minutes to open the scoring in the tie at Old Trafford, but Kaka made his mark with a dazzling double before the break.
A brace from Rooney including a stoppage time winner left the tie hanging in the balance heading to the San Siro and giving Ronaldo his chance to shine.
Inside one of football’s most iconic venues, the stage was set for the youngster to mark his arrival as an undisputed superstar.
Instead, he was one of many of United’s big names to fail to rise to the occasion.
Kaka set the tone with an early goal as the Italian side ran out 3-0 winners, stopping United’s European dreams in their tracks.
"Milan got their goals cheaply and that's disappointing," said Ferguson at full-time. "They were sharper and quicker to the ball and I think they've been good winners. We were on the back foot all the time and found it difficult.”
"In fairness, we never looked like we were going to score.”
After the game, Ferguson was asked about Ronaldo and did not hide his feelings.
“Cristiano had a disappointing night,” Ferguson admitted.
"He knows that but he is a young man and on nights like these he sees the professionalism and experience of AC Milan.”
Despite the disappointment, however, Ferguson urged Ronaldo to use the experience to his advantage.
“It is good to see where he has to go,” he declared.
Even after their Champions League disappointment, Ronaldo was a Ballon d’Or contender when the end of the year came around.
But after leading AC Milan to victory over Liverpool in the final, there was little doubt Kaka was the obvious winner.
Ronaldo leaped from 14th in voting the previous year to second but was no match for the Brazilian.
His inability to come out on top in their head to head duel ultimately proved costly with Kaka instead leading his side to the top prize on offer.
Immediately after defeat to AC Milan, Ferguson told his side: "You have to put disappointment behind you.
"They can win the title - we have to make sure they recover in the proper way.”
Ronaldo and his team-mates recovered to do just that, winning their latest domestic title.
But the Champions League was the one that got away whilst Ronaldo’s disappointment was compounded by the individual accolade which it cost him.
The following year, both parties came back with a vengeance.
The Portuguese sensation hit even greater heights and led the Red Devils to Moscow where they beat Chelsea on penalties to win the top prize in club football.
He also finished as top scorer in another Premier League triumph.
This time around, Ronaldo was the star, winning the first of five Ballon d’Or trophies by a huge margin.
He departed shortly after for Real Madrid for a world record fee and, 14 years later, he tasted Champions League heartache again for Juventus this week.
Elimination against Porto may have been one of Ronaldo’s most painful European nights since his trip to the San Siro all those years ago.
Ironically, it came in the week Manchester United and AC Milan will square off in competitive action for the first time in over a decade.
