The Red Devils were announced as one of the 12 founding clubs of the breakaway football competition set up to rival the established UEFA ran Champions League.
Yet the plans were met with widespread opposition from players, pundits and politicians - forcing all six English clubs involved to rethink their position and subsequent withdrawal.
In a turbulent 48 hours for football, which also saw UFC star Conor McGregor hint at launching a buyout of Man United, Woodward’s resignation signals an end of an era at Old Trafford.
Who is Ed Woodward?
Chelmsford-born Woodward is a former investment banker who helped the Glazer family purchase Manchester United in 2005, before joining the club as a financial planner.
It was Woodward’s first steps into the world of the beautiful game, leaving JP Morgan for one of football’s biggest clubs, where he has been ever since under different roles.
He was credited for doubling Man Utd’s commercial revenue in six years, from £48.7m to £117.6m, due to lucrative sponsorship deals with companies around the world.
Following the departure of CEO David Gill and manager Sir Alex Ferguson, Woodward was appointed executive vice-chairman as David Moyes took on the first team reins.
That summer transfer window saw United struggle to land player targets, with only Belgian midfielder Marouane Fellaini following Moyes from Everton to Old Trafford.
Fan unrest continued as Moyes was sacked 10 months after being installed as Ferguson’s long-term successor - at a time when Woodward’s influence was questioned.
Woodward went on to smash the world record fee paid for a player when Paul Pogba rejoined the club after four years away for £89m from Italian club Juventus.
Yet many supporters have criticised the fee paid for a player who has shown inconsistent form in a team which has failed to live up to the highs of the Ferguson era.
Why did Ed Woodward resign from Manchester United role?
The noise coming out of Old Trafford is that Woodward was due to leave his post in the summer, but his departure was announced early for the fear of leaks.
Yet the timing of the announcement would lend itself to the narrative of it being linked to the chaos surrounding the club’s involvement with the European Super League.
Woodward was understood to be heavily involved in the controversial ESL project.
A lengthy statement didn’t address the reasons for his departure, expected in the summer of 2021, but rather pointed to his successes during his time at the club.
His resignation took another twist when it emerged he had held talks at No.10 Downing Street days before the ESL announcement – yet it is claimed he was there to speak about Covid restrictions and fans’ return to stadiums.
Boris Johnson, who was one of the first people to condemn the breakaway league, was not thought to have been in the meeting, which didn’t discuss the controversial European Super League’s plans.
But Labour shadow culture secretary Jo Stevens has called on the minutes of the meeting to be released “to clear up any confusion and avoid accusations of hypocrisy”.
What has Ed Woodward said about resigning?
Woodward said he was “proud” to have served the club, that it was “well positioned for the future” and how he “desperately wanted the club to win the Premier League”.
He said: “The last 16 months have brought so many unique challenges and the club's work in the community and around the world during the Covid-19 pandemic has been heroic.
“The financial impact on football clubs has been severe, but United have been one of the most robust and resilient in the face of extraordinary financial pressures.
“I would like to thank United’s passionate fans for their support during the good and bad times. I know this has been a challenging period in our history, but your support for the team has never, ever been in doubt.
“Finally, it has been a pleasure to work with so many magnificent, talented and hard-working people.”
Man Utd co-chairman Joel Glazer, who was announced as vice-chairman of the ESL under latest plans, added: “Ed Woodward has served the club with great distinction.
“On behalf of everyone at United I would like to place on record our sincere thanks for his tireless work and dedication.
“His contribution to the club has been massive, and he will always be welcome at Old Trafford as a part of the Manchester United family.”
Who will replace Ed Woodward at Manchester United?
As the dust settles on the fallout from the European Super League and the planned resignation of Woodward, a replacement CEO is required to steer the Old Trafford ship this summer.
It has led to a host of names entering discussions from former players Edwin van der Sar and Darren Fletcher to personnel already at the club in Richard Arnold and Cliff Baty.
Van der Sar, the former Manchester United goalkeeper, will need tempting away from Ajax where he has steadily built a reputation in the administrative side of the game.
The 50-year-old knows all about success, having won the Premier League and Champions League as a player, and is still fondly thought of among the United fanbase.
Fletcher was appointed Man United’s first technical director in March after he was initially brought back to the club by manager Ole Gunnar Solskjaer as part of his coaching team.
Arnold has worked as commercial director for the past 15 years and is reportedly a close ally to Woodward and the Glazers, as is Baty who is the current chief financial officer.