Having spent in excess of £1bn across their opening three transfer windows, co-owners Todd Boehly and Clearlake Capital must find a way to ensure that they meet the Premier League's Profit and Sustainability regulations on June 30.
Reports maintain that club officials remain comfortable that they fill tick the necessary boxes, despite making losses of over £200m across the last two published periods.
In order to comply, Chelsea must not make a total loss of £105m across a three-year period, putting their hierarchy under pressure to get the books in order.
Thiago Silva's free transfer to Fluminense will get the centre-back's wages off the books, while £28m will be recouped from Lewis Hall completing his transfer to Newcastle United.
A £4m loan fee will arrive from Fulham for Armando Broja, while Chelsea are hopeful that the likes of Kepa Arrizabalaga, Ian Maatsen and Romelu Lukaku will all complete permanent transfers elsewhere.
Every little helps...
However, despite all that possible income, Chelsea are in a position where they require all the help that they can get in order to meet the rules.
According to The Telegraph, Chelsea will receive assistance on that front through a payment that will arrive from Real Madrid.
When Chelsea agreed to sell Eden Hazard to Los Blancos in 2019, it came with the possibility of £40m arriving courtesy of add-ons through Real's performances on the pitch.
Hazard has since retired, naturally resulting in Real not getting value for money from the €150m transfer, and it has been revealed that the Spanish side are still having to pay out money despite the Belgian bringing an end to his career.
The report says that Chelsea will receive £5m from Real courtesy of the La Liga champions reaching the Champions League final, where they will play Borussia Dortmund.
As it stands, it remains to be seen whether the extra income will prove to be a difference maker, but it certainly helps offset some of the big-money fees that Chelsea have shelled out in the past.
Chelsea are currently attempting to secure a sixth-placed finish in the Premier League standings, with there being roughly a £3m difference between each position.
That would also lead to a Europa League spot, which would generate more income in the future, but Chelsea still require one win from their final two games to guarantee a minimum of seventh.