Liam Rosenior's Chelsea side travelled to the Diego Armando Maradona Stadium in Naples looking to secure automatic qualification following their previous outing against Pafos FC, which proved to be an underwhelming performance and result.
Here's four things we learnt as they looked to bounce back in Europe, with only a win enough to see them through.
Last-16 looms
Starting the evening in eighth place in the table, the last automatic spot for progression, Chelsea were teetering on the brink of defeat at half-time but managed to turn the tie on its head, sending the home fans and former manager Antonio Conte away unhappy and Napoli out of the competition.
The 3-2 victory saw Chelsea rise up to sixth place in the table, as one of five English teams to make up the top eight; only Newcastle United have been left out in the cold to scrap it out for one of the remaining eight places.
Defensive gamble doesn’t pay off
Liam Rosenior rolled the dice and named a starting line-up that had a three man defensive back line, with Captain Reece James playing in a central defensive role. Despite the presence of more recognised players fitting the profile, such as Trevoh Chalobah and Jorrel Hato starting the match as substitutes.
Chelsea players leave the pitch at half-time 2-1 down | Photo Credit: Francesco Pecoraro via Getty Images
From the start, Chelsea's defence showed instability and a lack of confidence, and it was neither a surprise nor against the run of play when Napoli took a 2-1 advantage into half-time following goals from Antonio Vergara and Rasmus Hojlund. Snatching the lead from the West Londoners after an early penalty was converted by Enzo Fernandez to open the scoring, despite the visitors failing to create little in attack.
Reverting to a back four for the second half, Chelsea offered far more of an attacking threat and avoided conceding further.
Liam Rosenior has a lot on his mind as Chelsea struggled defensively in the first-half. | Photo Credit Tullio M. Puglia via Getty Images
Joao Pedro stands out
The standout player from Rosenoir's short reign is surely the Brazilian Joao Pedro, who has now bagged four goals in his last three starts and looks every inch the number nine that has so often alluded Chelsea. A couple of stunning goals in his first season in Europe's elite Cup competition should put him firmly in the sights of the Brazilian national team manager Carlo Ancelotti ahead of this summer's FIFA World Cup.
The improvement in his performances comes at a pivotal time in the season, with Chelsea still competing on four fronts in this campaign.
Ensuring the Blues avoid the hustle and bustle of the play-offs will come as a huge relief to the club's supporters and management, as they look to improve upon their domestic form and retain their place in this competition next season.
Joao Pedro is applauded by fellow Brazilians Estevao and Andrey Santos. | Photo Credit Chris Lee via Getty Images
Palmer provides
Another Chelsea player to secure a double last night was the returning Cole Palmer. Assisting both of Joao Pedro's second half strikes, he had an instant impact when coming off the bench.
Despite being deemed unfit to start the game, and having not featured in the weekend win against Crystal Palace, Palmer looked back to his best and appeared to have real chemistry and understanding when playing alongside Pedro.
Superstitious Chelsea fans will take heart from the fact that they staged a dramatic comeback against Napoli on their way to their victorious final back in 2012. When they also had seen a young, relatively inexperienced manager take the helm mid-way through the season, Liam Rosenior will hope that he can follow in the footsteps of Roberto Di Matteo and deliver success and silverware to Stamford Bridge.