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Animosity has been bubblingbetween the Premier League giants and European football's governing body for almosta decade now, and the latest clash has further strainedthe relationship.
Fans of City have made a habit of booing UEFA's anthem when it is played ahead of Champions League games, something that has intensified since 2014, when the club fell foul of Financial Fair Play.
The latest butting of heads could result in City losing their Champions League status and cost them hundreds of millions in the process -something that, if it comes to pass,will naturally not go down well.
So what exactly is happening on Monday? Goal brings you everything you need to know.
UEFA's Club Financial Control Body (CFCB) found Man City to be in breach of Financial Fair Play (FFP) regulationsand slapped the club with a two-year ban from UEFA competition, along with a €30 million (£25m/$33m) fine.
In its statement confirming Man City's punishment in February, UEFA said that it found the Premier League club guilty of "overstating its sponsorship revenue in its accounts and in the break-even information submitted to UEFA between 2012 and 2016."
The governing body added: "The Adjudicatory Chamber has also found that in breach of the regulations the Club failed to cooperate in the investigation of this case by the CFCB."
City immediately denied the CFCB's findings and initiated anappeal against the decision at the first opportunity, with club CEO Ferran Soriano emphatically declaring: "The allegations are not true. They are simply not true."
Soriano said that the club's representativesdelivered what theybelieved to be "irrefutable evidence" against UEFA's findings and it is now up to the CAS to make a decision on the matter.
UEFA's investigation into the matter was prompted by the publication of a number of allegations by German magazine Der Spiegel, which drew on documents said to have been obtained by whistleblowers Football Leaks, in 2018.
In May, three months after the punishment was confirmed,UEFA chief Aleksander Ceferin was somewhat evasive about the topic when asked about it by the Guardian in the context of the Covid-19 crisis, which had seen football across the world postponed.
When asked if UEFA still supported the sanctions against City, Ceferin said: "Look, the decision was made and now thecase is at the Court of Arbitration for Sportand CAS will decide.
"That’s absolutely all I can say, for two reasons. Firstly, the independent bodies made the decision, I didn’t, and secondly, I really don’t know the case well enough."
Man City's CAS appeal against UEFA's decision will begin on Monday June 8 and the hearing isexpected to last three days.
Representations will be made by both parties to a panel of three judges - one chosen by City, one chosen by UEFA and one chosen by CAS - in support of their respective positions.
While the hearing will last only a matter of days, final adjudications can take weeks. It is expected that the outcome of Man City's appeal will be known in three or four weeks' time.
Once the arguments have been heard, CAS will make a decision which will either: uphold UEFA's position, reject UEFA's position or mitigate the punishment.
If Man City are successfulin their appeal against UEFA's punishment, their ban will probably be rescinded and they will be free to compete in the Champions League should they qualify.
However, should the CAS uphold UEFA's interpretation, then the ban will remain in place and City will not be able to reap the rewards of their Premier League finish by qualifying for the Champions League.
In that scenario, City's place in the Champions League (assuming they finish, as expected, in the top four) will go to the team which finishes fifth in the division.
It is possible that a club such as Manchester United, Wolves, Sheffield United or Tottenham - who are all in the mix for European qualification - could benefit from City's difficulty, should CAS upholdUEFA's view.
If, in 2020-21, Man City finished in the European qualification spots, their place would also go to the next highest-placed team.
In some cases, where a ban is not overturned,the CAS mayrecommend that the punishment is reduced. So, for example,it may be considered that a one-season banis sufficient.
Should City lose the case, they stand to potentially miss out on around£150 million ($190m), when one considers revenue such as tournament prize money, TV money, sponsorship and so forth.
There could also be a knock-on effect in terms of personnel, both in terms of the stars currently at the club and potential recruits, as alluded to by Belgium boss Roberto Martinez when asked about Kevin De Bruyne's future at the club.
"Kevin is a winner," Martinez told beIN Sports. “I think he will weigh up everything before his decision.
"He will take into consideration if there is a ban in theChampions League, if the coachthat he has a fantastic relationship is going to stay at the club.
“As you can imagine, this is the moment that a player like Kevin De Bruyne is enjoying his best years and he's given them to Manchester City. But then you think, 'what's going to happen in the next four, five years?'"
This is effectively achieved bylimiting the net losses a club is allowed to make over a specified time period.
The apparent issue with regard to the Man City case, as detailed by UEFA,is the break-even requirement, which orders that clubs must balance their books over the course of a three-year period.
FFP was introduced in 2011 after being approved by UEFA in 2010
CAS is the Court of Arbitration for Sport, an independent body which is the highest authority in the world for the resolution of legal battles between sporting parties.
Known as TAS (Tribunal Arbitral du Sport) in some parts of Europe, it is based in the city of Lausanne in Switzerland and has been operating since the 1980s, with further reform in 1994.