And yet what should have been the crowning glory of his time at Everton ended in disappointment, acrimony and wounds that he will hope to heal when he makes his return to the competition in charge of the Premier League champions.
David Moyes's journey
Started his playing career at Celtic and finished it at Preston, where he played alongside young loan signing David Beckham in February and March 1995
Ten months after guiding Preston North End to the Division One play-off final, took over at Everton, replacing Walter Smith in March 2002
Handed Wayne Rooney his Premier League debut in August 2002 before selling him to Manchester United two years later for an initial £20m
Steered Everton to a fourth-place finish in 2005 and a place in the qualifying stages of the Champions League
Took Everton to the 2009 FA Cup final, where they lost 2-1 to Chelsea
Moyes has yearned for another crack at the Champions League, not simply to right that wrong but also to prove his pedigree on the European stage after unfulfilling treks to foreign soil at Everton.
This European experience, or obvious lack of it, was an unticked box - alongside his failure to win a trophy - when any questions were posed about his suitability to take charge at Old Trafford when Sir Alex Ferguson announced his retirement after 26 years as manager.
It is in Moyes' make-up to try to answer those questions from the past as he leads Manchester United into Europe. The attraction of pitting his coaching skills against the continent's finest minds only adds to the appeal.
And when he makes his way to the technical area at Old Trafford on Tuesday, he will be greeted by another Champions League coaching rookie - and a familiar foe from his Everton days.
Archive: Hyypia on life with Bayer in March
Former Liverpool defender Sami Hyypia enjoyed his share of successes as a visiting player at Old Trafford. Now he is entrusted with the task of guiding Bayer Leverkusen and is already showing the mix of intelligence, organisation and sound tactical sense that made him a figure of significance during a decade at Anfield.
Moyes will have plenty of reasons for wanting to ensure Hyypia does not enjoy his visit on Tuesday. They go beyond any desire for revenge on the Finn for helping Liverpool get the better of his Everton side so often in derbies.
He will not simply be motivated by an old sense of injustice but also by a determination to demonstrate that he is comfortable on this elevated stage. He has the confidence to believe he will succeed.
Moyes must also assume the responsibility of putting United back into Europe's elite group of teams. Their recent Champions League record confirms they are not part of a main power base that has shifted to Germany and Spain - in the shape of Pep Guardiola's Bayern Munich, Borussia Dortmund under the charismatic Jurgen Klopp, Barcelona and Real Madrid.
Bayern, Real and Barcelona will be the early favourites and Moyes faces a tough task to gatecrash that trio and make a meaningful attempt at bringing the trophy to Old Trafford for a fourth time.
It is a heavy weight on a manager whose Champions League experience extends to two qualifiers that ended in eventual defeat - but his predecessor Ferguson and United's hierarchy clearly he felt he had the ability and players to carry it.
It was part of the package that made Old Trafford so irresistible to Moyes. If he has any doubts about his lack of Champions League pedigree, he will not share them.
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