10 Biggest Regrets in Manchester United History

Manchester United has a long and glorious history, both at home and in Europe.

They are the most successful club in English football and some of the greatest players and managers in the world have called Old Trafford home.

But they have not been without fault. They have made many mistakes over the years, some bigger than others.

They say you should live life without regrets, but these are the 10 of the biggest regrets in Manchester United's history.

I have organised them in chronological order and only chosen ones from the last 50 years.

Selling Johnny Giles

When Sir Matt Busby sold Giles to Leeds United in 1963, he probably didn't think too much of it. After all, Leeds were in the second division at the time and Giles had failed to establish himself at United.

Giles felt he had been treated poorly and, according to his autobiography, John Giles: A Football Man, he told his wife he would haunt Busby.

This passion would drive him to become one of the most dominant players in football for years to come.

He would be the heartbeat of a physical Leeds United side that won promotion in his first season at the club, and would be a thorn in United's side for years to come.

He allayed his physical presence with a great footballing brain.

Brain Clough would say in Clough: The Autobiography that "Giles could grab hold of a match, tuck it in his back pocket and carry it around with him. He didn't need to find space, it was as if space found him."

It is rumoured (by Goal.com and others) that Busby would privately state that selling him to Leeds and not seeing his potential as a midfielder was his greatest mistake in football.

The Post-Busby Debacle

Sir Matt Busby was until recently, the club's greatest ever manager. His legacy is without question.

But the mess he left in his wake must surely be one of the club's biggest regrets, and was a huge reason we went 26 years without winning a League title.

When he achieved his lifetime's ambition in 1968, some say he lost the passion that had driven him for so long.

He endured a disappoint 18 months before, deciding it was time to walk away and let Wilf McGuiness replace him.

He would come back in 1971 before once again handing off the reins, this time to Frank O'Farrell.

He would be the first of many as the managers office at Old Trafford became a revolving door.

The problem was that try as he may, Busby could never fully let go of the wheel.

He became the ghost that walked the corridors, exerting influence and his sheer presence put huge pressure on whoever took the job.

It was not till Sir Alex Ferguson took over almost 20 years later that the club turned a corner.

While he had earned his right to stay at the club, I'm sure there are those who wish it had been a clean break when he left.

The Failure to Sign Paul Gascoigne

It is sad to think that this picture sums up the career of one of the most talented players England has ever produced.

I believe that had he signed for United, it would have turned out differently.

For Alex Ferguson, he is the one that got away and Gazza himself has admitted he made the wrong decision.

In 1988, the 21-year-old was the talk of England and was in high demand. Ferguson went off on his summer holidays with the deal seemingly sealed.

In an interview with Piers Morgan, Gazza told the story of how his change of heart came about.

On the road to Manchester to sign a contract, he got a phone call from Tottenham who offered him improved terms and offered to buy his parents a house. 

And so he continued down the M1 and Tottenham had their man.

His career would never reach the predicted heights and he would battle alcohol and depression for the rest of his career.

Given Fergie's track record with troubled youths, it is plausible to think that he may have been the man to help Gazza fulfill his potential.

It was probably the last time Fergie went on holidays before getting his man.

Almost Selling the Club to Michael Knighton

Many fans, now tired of the Glazer era, look back on Martin Edwards' ownership of the club with fond memories.

What they forget is that he tried to offload the club not once, but twice to buyers with questionable credentials.

Robert Maxwell came close to purchasing the club in 1984 but no one came as close as Michael Knighton in 1989.

Before the club kicked off their first game of the 1989-90 season, Knighton was unveiled to the fans with a fanfare normally reserved for big signings.

Kitted out in the club's colours, he proceeded to do some ball juggling on the halfway line before smashing the ball into the net in front of the Stretford End.

Within days, the club discovered he was all huff and no puff, as his financial backers were less than concrete and the purchase fell through.

To make this embarrassing affair even worse, Knighton was offered a place on the board and 30,000 shares in exchange for keeping quiet about the ordeal.

Waiting 6 Years to Sign Edwin Van Der Saar

In 2005, Fergie finally solved the problem position that had haunted United since the Great Dane Peter Schmeichal left the club in 1999.

In the six years between Schmeichel and Van Der Sar, we suffered through Mark Bosnich, Massimo Tiabi, Raymund Van Der Gouw, Roy Carroll, Tim Howard, Fabian Barthez, Ricardo and even Andy Goram.

How much easier would it have been if Fergie had followed through on his desire to sign Van Der Sar way back in 1999.

Fergie wanted him, but when he approached Martin Edwards, he found out he had a deal in place to sign Bosnich.

Fergie backed down and Juventus snapped him up. United ended up spending almost £15 million on 3 different goalkeepers in the space of 12 months.

Fergie eventually got his man in 2005 and he would quickly become a club legend and further fuel Ferguson's regret of not pushing for him in 1999.

Selling Jaap Stam

Not many people have drawn the ire of Ferguson and survived to tell the tale, but even Fergie admitted he got this one wrong.

"It was one of the mistakes I made—hopefully I haven't made too many—but that was one," is what the Scot is said by Goal.com to have told the Daily Mirror.

There were a number of issues that played into the deal but there is no doubt that Ferguson's personal feelings played into the decision.

Ferguson was reportedly furious with some of the content of his 2001 autobiography Head to Head. He alluded to some dirty dealings by Ferguson and belittled some of his teammates.

Ferguson insists he was sold because he got an offer he couldn't refuse for a 29-year-old, who was coming off major surgery and had lost a step.

Stam would remain one of the top defenders in Europe for a number of seasons and United had to suffer through Laurent Blanc for 12 months.

Engine Room Issues

People highlight Manchester United's issues in midfield as if it is some breaking news story. What they fail to mention is that it's been United's problem for almost a decade.

Since they signed Juan Sebastian Veron in 2001, Ferguson has been trying to find long-term replacements for Roy Keane and Paul Scholes.

What is amazing is that despite the turmoil, United have enjoyed one of their most successful decades.

Of all the midfielders that United have signed in the last 10 years, only Michael Carrick has found a significant role. And even he has drawn huge criticism, wrongly in my opinion, from the club's fanbase.

Veron was the first but was followed by the likes of Owen Hargreaves, Kleberson, Anderson, Rodrigo Possebon, Carrick and the man so good they named him twice, Eric Djemba-Djemba.

Things got so dire last season that the club was forced to bring the 37-year-old Scholes out of retirement.

Ferguson will surely want to fix this problem before he hands over the reigns, so hopefully this season's signings Shinjo Kagawa and Nick Powell will provide part of the solution.

Allowing Ferguson Get into Bed with Magnier and McManus

When Irish business men JP McManus and John Magnier bought into Manchester United, Sir Alex Ferguson must've been licking his lips.

They were, after all, on friendly terms, and the size of their share in the club would surely increase his control.

Things ran smoothly for the first couple of years but that changed with a dispute over the ownership of the much vaunted horse, Rock Of Gibraltar.

Gifted a 50 percent share in the horse in 2001, Ferguson thought he had hit the gravy train as the horse's legend grew.

A relative novice to the murky world of horse racing, Ferguson mistakenly thought 50 percent ownership meant 50 percent of everything, including the potentially lucrative breeding rights.

McManus and Magnier had other ideas and Ferguson found himself in court.

The dispute found its way into the boardroom at Old Trafford with the Irishmen calling for Ferguson to be sacked.

Magnier and McManus had long been the men keeping the sharks at bay but the incident soured the relationship.

A now famous Florida businessman had been steadily building up his share of the club and pounced on the opportunity to buy out his Irish colleagues.

Their 30 percent stake gave him the leverage to launch his now infamous hostile takeover of the club.

That man's name? Malcom Glazer.

Not Shutting Up Shop Against Everton

As the saying goes, "live by the sword, die by the sword," and on the April 22, 2012, United died by the sword.

Chasing a win that would edge them ever closer to their 20th League title, United found themselves 4-2 up against Everton with 10 minutes to play.

A win would've left them six points clear of rivals Manchester City with just three games to play. If ever there was a case for shutting up shop, this was it.

Driven by the long-held ideal of playing attacking football, Ferguson refused to kill the game. 

Combined with the youthful exuberance of his team, this was disastrous. United went in search of a fifth goal.

Rafael and Evra combined to come withing inches of scoring only for Everton to counter attack and expose United at the back and make it 4-3.

Once the momentum had shifted, United were in trouble. Everton would score a fourth and United dropped two points.

Suddenly, City were only three points behind. Cue derby defeat at the Etihad and Man City were back in the driving seat.

Losing out on Lucas Moura and Eden Hazard?

When Alex Ferguson chases a player so aggressively, it is a given that he has bags of potential.

He made no secret this summer of his desire to land first Eden Hazard and then Lucas Moura, only to see both players slip through his grasp.

In the new landscape of European football, United are no longer at the top table financially. They have been replaced by the the Oligarchs and Middle Eastern Oil Barons.

We can only hope these players don't come back to haunt us in years to come.

That said, the last time we chased a talent playmaker and missed out, we settled for a little known 18-year-old from Sporting.

118 goals, multiple assists and £90 million later, United fans had no reason to regret missing out on Ronaldinho.

History has a funny way of repeating itself; lets hope that's the case this time around.