It was on August 26, 2014, that Manchester United suffered one of the most embarrassing results of their modern history.

After failing to win either of their opening two Premier League matches of the 2014/15 season, a League Cup tie against MK Dons represented a golden opportunity to get a first win of the Louis van Gaal era on the board. Instead, a much-changed United XI was cut to pieces, losing 4-0 at Stadium MK.

However, United, at least temporarily, had managed to put a smile on the faces of their supporters earlier that day, smashing the British transfer record to sign Angel Di Maria from Real Madrid. He had joined the club for £59.7million.

The Argentine had spent six years in the Spanish capital, making 190 appearances, scoring 36 goals and winning six major honours. He was United's fifth signing of the summer and their most eye-catching by some distance.

They had sourced themselves one of the most exciting wingers in world football, who Van Gaal described as 'world-class'. He was also handed the iconic No.7 shirt at Old Trafford.

After making his United bow in a goalless draw away at Burnley just four days after putting pen to paper on a five-year deal, Di Maria made his mark on his home debut, scoring directly from a free-kick ahead of providing the assist for Juan Mata to score in a 4-0 win over QPR.

Goals against Leicester City and Everton soon followed, meaning he made a flying start to life in England. His first six Premier League appearances saw him score three goals and chalk up four assists.

However, the honeymoon period did not last long. A move that initially resembled something of a coup quickly turned into a disaster.

After scoring a third goal in his first five United appearances against Everton on October 5, Di Maria did not find the net again until United made the long trip to Yeovil Town in the third round of the FA Cup in January. His case for making a mark in England, however, was not helped by the fact Van Gaal failed to deploy a system that suited him.

The Dutchman, who left Old Trafford in May 2016, preferred a midfield diamond that lacked width, denying Di Maria from playing in his natural role and producing the magic he had so often served up at the Bernabeu. Furthermore, he also found it generally difficult to settle in England, impacted by an attempted burglary on his home in February 2015.

His former United teammate, Wayne Rooney, said: "He could have been a major star at United but at the time we were going through a bit of a transition and it was tough for him to settle. He had young kids and lived a couple of houses down from me and someone tried to burgle him. I remember that really shook him and his family. From then on, really, you knew it was going to be tough for him and it was probably better for him to leave."

The Argentine's relationship with Van Gaal had also took a battering. Despite waxing lyrical about the Dutchman upon his arrival in Manchester, it was not all that long before there was friction between them. Van Gaal, Di Maria later revealed, was regularly showing him negative clips of his performances, resulting in them clashing.

"I was at Manchester and everything was fine with Van Gaal during the first two months," he told ESPN Redes in Argentina. "After one fight, things weren't the same. The relationship wasn't the same.

"The fight with Van Gaal occurred because he was always showing me bad and negative things and all that held me back. One day I fought with him. I told him I didn't want to see those things anymore, that I was doing things well and asked him why he wasn't showing me good things.

"He did not like how I spoke to him and from there the whole problem started."

Despite clashing, Van Gaal refused to freeze Di Maria out of the picture like a lot of managers would have done. His minutes on the pitch, however, did reduce, resulting in him failing to start any of United's last 10 Premier League games of the season. His final league start for the club was against Newcastle United at St James' Park on March 4, just days before he was sent-off in a 2-1 home defeat to Arsenal in the FA Cup.

In a separate interview, Di Maria described Van Gaal as the 'worst coach' he has ever crossed paths with, saying: "My problem at Manchester was the coach. Van Gaal was the worst coach of my career.

"I would score, assist, and the next day he would show me my misplaced passes. He displaced me from one day to the other, he didn’t like players being more than him."

Come the 2015 summer transfer window, it was no surprise when Di Maria exited Old Trafford less than 12 months after arriving, leaving to join Paris Saint-Germain. After a period of frustration in England, he flourished in the French capital, scoring 93 goals and creating 119 in 295 games across a seven-year period.

Whether Van Gaal's negativity towards him was the driving force behind resurrection or not, he delivered the goods in the same way United had hoped he would have. Now 36 and back at Benfica, he will go down as one of the best players of his generation, even if his 12-month stint at United was a forgettable experience.