The Russian billionaire has now overseen eight managers at Stamford Bridge, and is currently searching for lucky No. 9.
Who will land the Stamford Bridge gig? Here's the top five contenders...
The Spaniard won two league titles and a UEFA Cup with Valencia, an FA Cup and a Champions League at Liverpool and a Supercoppa Italiana and FIFA Club World Cup with Internazionale.
Clearly, Benitez has a winning pedigree. The 52-year-old—who has been without work since December 2011—also claims he has been biding his time "for a top side that can challenge for trophies" (via The Guardian).
Furthermore, according to The Daily Mail, Rafa is open to a short-term deal that would pave the way for a man such as Pep Guardiola in the summer.
He could also be the man to rouse Fernando Torres from his goal-scoring slumber.
However, Benitez has fallen out with assistant coach Pako Ayesteran, the man who was at his side during his success at Valencia and Liverpool. Some argue that his powers have been weakened by Ayesteran's departure.
Despite having held just one senior coaching position, the former defensive midfielder is understood to be the top name on Roman Abramovich's managerial wish list.
After achieving 14 trophies in four seasons with Barcelona (making him their most successful manager of all time) with tiki-taka flair, it's easy to see why his services are so desirable.
However, a man who takes a break from the game at the height of his powers may not be easy to coax back into the thick of it. The Guardian's Spanish expert, Sid Lowe, believes Guardiola will make Chelsea wait for his arrival, if he even decides to come at all.
Having been linked with jobs everywhere from Southampton to Ukraine (via EuroSport), the press would have us believe everyone's favourite not-a-wheeler-dealer manager has been in contention for the Chelsea job since the summer.
The East Londoner did a phenomenal job of getting Tottenham into the Champions League, but his honor roll peaks with an FA Cup with Portsmouth and an Intertoto Cup with West Ham—and is marred by relegations with Bournemouth and Southampton.
Ultimately, Abramovich may be looking for someone with a more polished resume than 'Arry.
The Special One enjoyed a 70.8 percent win rate while with the Blues—a feat bettered only by Guus Hiddink in his short tenure—and won two leagues, two League Cups and an FA Cup.
In May, Mourinho signed a two-year contract extension that should keep him at the Bernabeu
until June 2016. This effectively rules him out of the Chelsea job, but the €15 million compensation Abramovich paid Porto for Andre Villas-Boas shows the Russian is not afraid of breaking a contract to get his man.
Mou has confirmed his desire to return to the Premier League to face Sir Alex Ferguson as an adversary before he retires. He'll get no better chance than taking the reins at Stamford Bridge once again.
If Abramovich cannot land a young precocious Spaniard named Pep Guardiola, many believe he could opt for a young precocious Spaniard named Unai Emery.
The 41-year-old has been linked with the Blues job since his successful spate at financially troubled La Liga outfit Valencia.
However, Emery was lured to Spartak Moscow in May by another Russian billionaire Leonid Fedun. Abramovich has worked with his oil magnate counterpart before—reportedly teaming up to financially reward the Croatian national team for Euro 2008 qualification—but Leonid may not be inclined to release his new coach in the near future.