Defeat could cost Maurizio Sarri his job, and the assignment couldn’t be tougher, against Pep Guardiola’s rampant, quadruple-chasing Manchester City. A side which thumped the Blues 6-0 less than a fortnight ago.
Sarri hit the ground running when he arrived at Stamford Bridge, unbeaten in his first 18 games in all competitions, revamping the Blues midfield in the process around new signing Jorginho.
But Sarri’s fruitful start to life at Chelsea has quickly turned sour – the impact of the Italian in midfield is being nullified and Chelsea has suffered.
Tottenham, Arsenal and, most recently, Manchester United have unlocked the secret to stopping Chelsea, using their attacking midfielder to man-mark Jorginho and stifle his distribution.
Delle Alli did the job for Spurs in their 3-0 win over the Blues in August, Aaron Ramsey was Arsenal's secret defensive weapon in its win over the Blues and on Tuesday (AEDT) and Juan Mata took the assignment suit for Manchester United, neutralising the link between Jorginho and Chelsea's centre backs.
Chelsea’s FA Cup defeat to United came off the back of three defeats in its last five Premier League games, but Sarri's side gave its manager some much-needed, albeit temporary reprieve easing past Malmo in the UEFA Europa League to book its place in the round of 16.
Sarri has to get the job done against City in the Carabao Cup on Monday (AEDT). City boss Pep Guardiola is undoubtedly aware of Chelsea's achilles heel in midfield, and Sarri has to find a way to counteract this if he is to have any chance of winning some much-needed silverware.
Due to Manchester City's expected high press, the Blues could find more joy playing out from the flanks, allowing Jorginho to receive the ball higher up the pitch and with a little more time and space.
A win on Monday is crucial for Sarri to win back some support - with fans growing tired of unfavourable results and reports of player unrest, he sits in a precarious position at Stamford Bridge.
The 60 year-old has turned the heat back on his players, with several animated public rants, which won’t please club owner Roman Abramovic – a man you don’t want to disappoint.
Since the Russian took over in 2013, 14 managers have come and gone - the same number the club had in the 97 years prior. An ever-present axe hangs over every Chelsea manager and Sarri is no different.
The journeyman desperately needs to win on Monday, or he could be on the lookout for his 20th club. It may be unlikely, but it's certainly not impossible - it's Sarri's biggest test and his opportunity to prove his worth.