The coach's short and turbulent reign was ended by chairman Daniel Levy on Tuesday, with the former midfielder having alienated a number of senior Spurs players.
Sherwood, having played a role in the departure of manager Andre Villas-Boas a week earlier, promised the chairman wonderful, attacking football and a return to the glory days of old. He convinced him that the squad was far better than had been shown under his Portuguese predecessor. He vowed to lead the club into the Champions League.
Given his work with the youth development squads – where youngsters such as Nabil Bentaleb were groomed for the first team – and having fostered a close working relationship with Levy, Sherwood appeared the perfect man to take the club forward. The chairman was convinced Sherwood shared his desire to get the best out of his expensively-assembled squad and to promote the youngsters coming through the club's impressive academy.
In fact, word through the club spread that perhaps a diamond in the rough had been found, a young manager with exciting ideas capable of becoming Spurs' very own Pep Guardiola.
Within two months, however, cracks appeared. As Sherwood's ideals and approach began to clash with the club hierarchy, so the board's failure to back the new manager publicly and unequivocally served to fuel his feeling that he was unable to do his job properly from such an undermined position.
Despite overseeing a series of positive results – including a 2-1 win at Manchester United – Sherwood had swiftly concluded, despite his previous assurances to the contrary, that the players were not good enough. Despite resisting Levy's urge to enter the January transfer market only weeks previously, Sherwood was soon expressing his concerns that the squad he was given to work with was not good enough to achieve a top-four finish.
Having set out to play a high-intensity pressing game, not dissimilar to the one employed by his potential successor Mauricio Pochettino at Southampton, he lobbied Levy to buy players to suit his vision, such as Romelu Lukaku, whilst asking for stars such as Paulinho and Roberto Soldado - bought only last summer - to be sold.
Such was his frustration, the 45-year-old began to lock horns with senior players in the Spurs dressing room. An abrasive character both on and off the pitch, Sherwood's old-school management style – favouring screaming and shouting over conciliating – did not sit well with some senior international players within the squad. Over time, his approach began to be interpreted as dismissive and arrogant.
Despite derision amongst several senior players, Sherwood's approach with Adebayor paid off and the striker recently expressed his hope that the "great man" would be given a chance to manage the club beyond this season.
"No matter where he goes, I will always keep him in my heart and I have a huge respect for him," said Adebayor recently. "He respects everyone equally, and for me he is a great man and a great manager."
His handling of the club's youngsters also blossomed. Having worked with the academy previously, Sherwood promoted a handful to the senior squad – Bentaleb and Harry Kane the most notable – and immediately drafted them into the first team, believing they were the men best suited to carry out his instructions on the pitch. Under his watch, a host of young talent flourished in the first team.
But not everyone in the dressing room felt as closely tied to the manager.
Eventually the apathy amongst some players was fed back to Levy, who became aware that some individuals were non-receptive to Sherwood's ideas. Levy had already grown concerned by Sherwood's handling of agents during the transfer window – some of whom he had no interest in building relationships with – and was disappointed with a number of his press conferences, where his forthright and honest delivery ruffled too many feathers for the chairman's liking.
Such an approach came to a head following Spurs' 4-0 thumping at the hands of Chelsea in March. Heading inside to face the cameras, Sherwood let rip in an astonishing rant at the club's players. "There's a lack of characters in this squad, too many of them too nice to each other. It hurts me and I won't forget about this when we hit the motorway - but some might.
"You won't finish in the top four if you don't beat top teams. You're miles away unless you beat the top teams. There have been too many blips. The club talks about fourth. Wake up."
The well-publicized dressing down of his players did not go down well, prompting a chairman-manager meeting on the Monday after the game. Despite a mini upturn in form, Sherwood's words sowed the seed of deep ill-feeling within the squad and upper echelons of the club.
Thereafter, although he had been given an 18-month contract, Sherwood was aware his days at White Hart Lane could well be numbered. Impassioned press conferences regarding his Spurs record have been aimed at prospective employers rather than at convincing Levy he is the man to take Tottenham forward.
He has been resigned to his fate for some time, with a number of managers linked with the hotseat.
Sherwood felt undermined during large periods of his spell at White Hart Lane, with Pochettino, Louis van Gaal and Rafael Benitez all linked with the hotseat. "I'm like a supply teacher," he noted last week. "I am doing this job with a lot of uncertainty around my future.
"My situation is that you have got players talking about me not being here next season. That's how difficult the situation is to keep the players [in line]. It's natural. If they knew I was here for five years or three years or, certainly, for next year, then they wouldn't be saying that, would they?"
Despite his turbulent spell in north London, though, he is convinced he is a good coach. Having steered Spurs to a sixth-placed finish – albeit 10 points off fourth-placed Arsenal – he believes he did a good job this season and is sure his future lies in management. Indeed, he is already eyeing up potential job opportunities.
Yet, for all his talk and all his promises, the marriage of Tottenham and Tim Sherwood just did not work out. A good talker, Sherwood allowed his own words to trip him up once too often, having promised Champions League football and delivered only Europa League qualification, achieved with an often unhappy squad.
For Levy, what appeared to be an opportunity to exorcize the ghosts of managers past turned into something of a nightmare. Sherwood had to go, according to the chairman, and only now can the rebuilding job begin.