Chelsea are set to face even more questions about their success under former owner Roman Abramovich after leaked documents appear to show a string of payments that potentially breached Financial Fair Play (FFP) rules, as well as other strict laws of the game.

Through a joint investigation by the Guardian and a group of international outlets including the Bureau of Investigative Journalism (TBIJ) and Germany’s Paper Trail Media, files have been uncovered relating to a series of payments spread out over a decade worth tens of millions of pounds.

These payments are reportedly 'routed through offshore vehicles' which belong to the Russian billionaire, who was forced to sell the club in 2022 after the Russian invasion of Ukraine saw sanctions imposed on his UK assets. The transactions are believed to be for Chelsea's benefit, with some questioning whether the governing bodies were made aware of the accounts.

Those that benefitted from the payments appeared to include the agent of Chelsea great Eden Hazard, who retired just last month, an associate of the title-winning manager Antonio Conte and Chelsea FC officials. Last month, the Blues' acquisition of both Willian and Samuel Eto'o also came into question after it was revealed that a company owned by Abramovich also made payments that appear to have benefited fellow Russian billionaire Suleiman Kerimov, the owner of Anzhi Makhachkala whom the pair played for.

In just two days, the Cameroonian striker and the Brazilian winger joined the Blues, although the latter was in controversial fashion as Willian had all but written his signature on a contract with Chelsea's bitter rivals Tottenham. However, one phone call from Abramovich to Kerimov later and he arrived at Stamford Bridge the next day.

It was then revealed that two months prior to the deals, the Abramovich-owned Leiston Holdings had paid two companies connected to Kerimov for "services in […] relating to football, including scouting and other football-related advice". According to the Guardian, experts now believe that the Blues face a points deduction as a possible penalty for the dealings.

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The club's finances are already under examination by the Premier League, with their investigation overlooking a period of seven years from 2012 until 2019, after which the new ownership, including BlueCo.'s Todd Boehly, voluntarily reported that they'd found that 'incomplete financial information' had previously been submitted under Abramovich.

The Football Association have confirmed that they're investigating the club over that matter while UEFA have already fined Chelsea £8.6m over the admission, but now can't look at any evidence from before 2020 due to restrictions within its own laws. Another example of a potential deal that benefited the club was on July 18, 2017 through a company called Conibair Holdings.

Being an Abramovich-owned company based out of the British Virgin Islands (BVIs) in the Caribbean, they signed an £10m agreement with Federico Pastorello, an Italian football agent, for a 75% stake in Excellence Investment Fund (EIF), a business based in Delaware in the U.S.

Pastorello is reportedly close with former Blues manager Antonio Conte, and has previously spoken about the manager's contract negotiations to the media. Well, coincidentally (or not), Conte just so happened to sign a new two-year deal with the club worth £9.6m that same day.

The Guardian claims 'four leading sports lawyers' have told them that some of the payments may have broken both Premier League and UEFA regulations in regards to FFP, with football finance expert Kieran Maguire claiming that a financial penalty or burden is less likely than a points deduction on Mauricio Pochettino's side.

He said: "If there is proof that the club has used third party transactions to circumvent the profitability and sustainability rules then sanctions would be either financial or a points deduction.

"The latter is more likely as any commission investigating a club’s circumstances will want to put out a deterrent that dissuades others from repeating such behaviour."

With the Blues seeming to get back on their feet under the Argentine in recent weeks, with big results against Spurs and league leaders Manchester City, this could be a hammer blow to their chances of achieving Champions League football for next season. While it's believed teams that finish in fifth will be able to play on European football's biggest stage next season, the likelihood of Chelsea reaching that goal whilst under a points deduction is slim given the amount of competition they face for the spot.