A closer look into how Manchester United’s relationship with Real Madrid has gotten increasingly strained over the years.

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Spanish left-back Sergio Reguilon is heading to the Premier League but will be joining Tottenham Hotspur and not Manchester United, as had been widely speculated for most of the transfer window.

The Red Devils seemed in pole position to secure Reguilon’s signature but were unwilling to meet Real Madrid’s asking price and their condition of including a buyback clause for the player – which proved to be a major stumbling block in the deal between the clubs.

Spurs’ acceptance of Madrid’s terms paved the way for a swift deal for Reguilon, leaving United a bit red-faced and with the feeling of being used to entice more bidders for the player.

It isn’t the first time United have been left in this position by Madrid and history suggests that it won’t be the last. The truth is the Red Devils and Los Blancos haven’t been on the best of terms for some time now and this latest episode is just another reminder of that.

The seeds of mistrust

The souring of the two football giants’ relationship, in fact, can be traced all the way back to 2008 when then United manager Sir Alex Ferguson took offence to nature of Madrid’s pursuit of Cristiano Ronaldo.

Unimpressed by the tactics used by Madrid to lure Ronaldo to the Bernabeu, Ferguson labelled the Spanish heavyweights as the ‘mob’ and said that ‘I wouldn't sell them a virus’ let alone Ronaldo.

Ultimately Ferguson managed to ward off the Spanish outfit’s interest for another year before Ronaldo joined Los Blancos for 80m pounds – then a world record transfer fee – in 2009. It was here that seeds of animosity between the two clubs started to grow.

Fasttrack to 2013 in the post-Fergie era and the relationships between the two began to get even more strained following the last-minute collapse of a move that would have seen Portuguese left-back Fábio Coentrão join United from Madrid.

The next episode in the already fractured relationship between the two teams came in the form of Angel Di Maria, who Los Blancos were eager to get rid off from their books despite the Argentine's dazzling display in their Champions League triumph.

Sensing the mood at the Spanish capital, Di Maria was ready for a move away from the club and wanted to join Paris Saint-Germain. However, Financial Fair Play (FFP) regulations meant that it wasn’t possible for PSG to bid for Di Maria in that transfer window.

As a result, Di Maria was shipped off to United and in hindsight, it now looks like a stop-gap both Real and the Argentine were possibly aware of. Di Maria would go on to spend just 12 destabilizing months at Old Trafford before joining PSG in the following summer to leave United and their fans with a bitter taste on the tongue.

A dodgy fax machine

However, the tipping point in the relationship between the clubs came in the summer of 2016 when United goalkeeper David de Gea looked destined to join Real only for a deadline day collapse due to paperwork not being submitted in time, which has since been infamously blamed on a faulty fax machine.

The cold stand-off between the two clubs only intensified over the next summer when United outbid Real to sign French midfielder Paul Pogba, who had long been on Los Blancos’ radar.

Real captain Sergio Ramos’ future was another flashpoint in the tumultuous relationship between the teams. While angling for a salary hike and contract extension at Real, Ramos made it clear that he was ready to join the red side of Manchester.

Reguilon not the first Sergio that got away

It even looked like he was United-bound at one stage, but Real came good at the last minute and secured their captain’s future to leave United a bit embarrassed and with the feeling of being used solely for the purpose of getting a better deal.

"There was an offer from United," Ramos told COPE. "I considered changing for a while but Real Madrid was always my priority and there were no economic reasons."

That feeling seems to have resurfaced in the ongoing transfer window with another Sergio who is on Madrid’s books. United for the longest part looked like they were to get their man but once again Real seem to have played their hand perfectly.

Not only will Spurs meet Madrid’s asking price of 30m euros for Reguilon, they have also agreed to insert the buyback clause that Real wanted in the contract – a major obstacle to the deal for United.

With Reguilon now London-bound, it’s important for United to ask themselves if it’s worth being dragged into business with Madrid. Going by their past record, the Red Devils have been used to drum up interest for Madrid and their players more than once.

Reguilon is merely the latest chapter in a long and dodgy recent past that the clubs share. United will do well to finally learn from this experience and ensure that they don’t continue repeating their naïve mistakes while dealing with Real Madrid – a club which unlike United is way more competent in dealing in transfers and contract extensions behind the scenes.

Feature image courtesy: AFP / Lars Baron