Manchester United face Atletico Madrid boss Diego Simeone for the first time ever in the Champions League Round of 16 tie.
The Argentine has spent over a decade at the helm of the Spanish capital club, whom he has transformed from an underperforming sleeping giant into one of Europe’s most powerful clubs.
Simeone has been suggested as a possible long-term coach at Old Trafford and most recently following the sacking of Ole Gunnar Solskjaer earlier this season.
Alongside goalkeepers David De Gea and Jan Oblak could have been lining up on the opposite sides had negotiations over a swap deal gone through, Simeone’s position is one of the most interesting aspects of this European tie.
The Argentine has worked minor miracles at the Spanish capital club, whom he has transformed from perennial underachievers into one of Europe’s best teams.
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Under Simeone, Atleti reached two Champions League finals and last year’s La Liga title was their second under his guidance.
Yet things are not going to plan for the coach and the club this season – they languish outside of La Liga’s top four, are out of the Copa del Rey and are underdogs for the Champions League tie against United.
There have been suggestions that this could be the beginning of the end for Simeone in the Spanish capital – although of course it may be too early to write off such a distinguished coach.
The Argentine may well be available this summer, which would coincide with United’s search for a new coach and to which he may enter as a surprise outside candidate.
It would not be the first time United attempted to pursue Simeone and as outlined by The Times, Simeone was a major candidate at Old Trafford for replacing David Moyes in the position in 2014.
At that time, the former midfielder was guiding Atleti to a sensational league title ahead of Real Madrid and Barcelona, while also steering them to their first ever Champions League final as they eliminated Chelsea in the semi-finals.
The linguistic differences have always provided the biggest stumbling block to Simeone managing in the Premier League and it now appears unlikely he will ever move into English football.
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Communication is such a large part of his managerial style and it is unlikely he would have been able to successfully convey his messages to players without a sound grasp of the English language.
It was in 2014 when Simeone began taking English lessons, which initially gave United hope but they were aware of the complications of luring him out of Atletico Madrid – so eventually opted to appoint Louis van Gaal instead.
The reality is that by 2014, it was already probably too late for United or any leading English club to tempt Simeone – who has gone on to build somewhat of a dynasty at Atleti.
That proved to be a significant crossroads moment for both clubs and Simeone himself, while another huge turning point for all three parties is likely to re-emerge in the months to come.