Saddled with the stigma of replacing club legend Roberto Di Matteo and his Liverpool past, Benitez vowed to win over his critics with victories and silverware.
But he has since presided over shock defeats in the Club World Cup and the League Cup, as well as allowing Manchester United to shatter any lingering Premier League title hopes by extending the gap between the two clubs from four points to 11.
Despite these setbacks, Pep Guardiola’s decision to reject Roman Abramovich’s overtures in favor of a move to Bayern Munich has sparked suggestions Benitez could be handed the reins beyond this summer, although the Russian and his advisers are keenly aware of the fan uproar such a decision would create.
Yet while he concedes failure in Japan has dealt a bitter blow to the Spaniard’s hopes of keeping his job, Hasselbaink - who scored 88 goals during a stellar four-year spell at Stamford Bridge - believes Chelsea must first decide on an identity before choosing a new manager.
"It’s always going to be difficult to replace a hero, as Robbie Di Matteo was, and someone who has won the Champions League," Hasselbaink told Goal.com. "That’s what Benitez has got against him, and then there’s also the Liverpool effect. The only thing that’s going to help him is results, results, results. It didn’t help that he didn’t win the Club World Cup, a competition you can only get in if you win the Champions League. It’s not something you’re going to play in every year, so that was a big blow.
"You have to look at what Chelsea’s plans are for the next five to 10 years. What do they want? Where do they want to go? What kind of style do they want to play? What kind of club do they want to be? There have been a lot of changes over the last couple of years, so you have to look at those things and then decide whether Benitez will fit into that. It’s difficult to say whether he’s the right man for the long term."
Fernando Torres, too, has become a lightning rod for criticism during Benitez’s reign. Despite a well-taken equalizer against Brentford on Sunday, the 50 million pound man was booed by Chelsea supporters against Swansea and Southampton, and the sense is he has reached the end of their patience.
Hasselbaink, however, insists such treatment is counter-productive, and still thinks Torres can come good. "I personally don’t like fans booing their own players," he added. "That’s not right.
"Whatever they say, I think every time Torres puts the Chelsea shirt on he is doing his best. He’s struggling with confidence, especially because he knows everyone is watching him.
"It’s not an easy situation, but he’s the only one who can help himself out of it, and only scoring goals will give him confidence. If he goes on a run of scoring 10 goals in 10 games, and important goals, everything will be forgotten.”
Torres’ ongoing struggles have led many to suggest Chelsea were too quick to discard Didier Drogba in the summer, but Hasselbaink believes the Ivorian left Stamford Bridge at the right time, and is confident the January arrival of Demba Ba from Newcastle will help fill the void.
"I think Didier left on a good note," he continued. "Having won the Champions League final, he was due a new challenge. I was surprised when I heard he’d gone to Galatasaray, but Turkey is an up-and-coming league. Wesley Sneijder has gone there, and they’re always looking to get new stars, so in that sense it’s not hugely surprising.
"Demba Ba was the buy of this window. Paying 7m pounds for a goalscorer at this time is not a lot of money in many ways. It was a very shrewd."
A former Atletico Madrid striker himself, Hasselbaink has been keeping a keen eye on Radamel Falcao, scorer of 18 goals in 18 La Liga matches this season.
The Colombian sensation has been heavily touted as Torres’ replacement but, while he believes the 26-year-old has the game to succeed anywhere in the world, the Dutchman maintains Chelsea have more fundamental choices to make before they decide whether to splash 50m pounds on another striker.
He continued: "He's got something about him. His aura is just finishing, scoring goals. He’s always in the right position, on the shoulder or in the box, and he doesn’t think twice about having a shot. He’s very resolute, and I think he would score everywhere.
"But again, it depends what the plans of Chelsea are for the next couple of years. Do they want to buy young players to develop, or do they want to buy players to challenge for the Champions League and the Premier League year-in, year-out, because they would have to be more established names. It’s all about where they want to go."
Jimmy has recently teamed up with Jermain Defoe, Jermaine Jenas, George Boateng, Billy Sharp and a number of other players to help young people connect to opportunities on www.slenky.com.
To celebrate the launch of the Slenky App on the new BlackBerry 10 Slenky are giving away a BlackBerry Bold 9900! For your chance to win simply enter here: https://www.slenky.com/competition/4