The youth development coach, promoted to run the team after the sacking of Andre Villas-Boas on Monday, looked like making a dream start by leading Spurs to the semi-finals of the Capital One Cup.
His bold move in recalling Emmanuel Adebayor from exile and reverting to a 4-4-2 formation looked to have paid off when the Togo striker scored a spectacular first goal of the season in the 66th minute.
But it all went horribly wrong thereafter when West Ham spoiled the party and booked their place in the last four against Manchester City with two goals in the space of four minutes — Matt Jarvis equalising in the 80th minute and then Modibo Maiga grabbing the winner with his first goal in more than a year.
By the final whistle it was West Ham fans celebrating, and Tottenham’s supporters going home wondering whether Sherwood’s brave new world will be any better – or last longer, than Villas-Boas’s ill-fated reign.
While a raft of names have been floated as the next manager, Sherwood has been told the job is his if he can make a convincing case for it.
And it looked to have started so well. Once the former club captain had taken his seat and the inevitable phalanx of photographers cleared, he didn’t waste any time showing how much he wanted the job on a permanent basis.
With Tottenham’s more direct approach, there were plenty of balls into the West Ham penalty area, but the goals would not come. Adebayor was called in from the cold to partner Defoe in a 4-4-2 formation that Villas-Boas would never countenance.
Daniel Levy and his sporting director Franco Baldini had asked Villas-Boas to consider a more attacking approach and a different shape to his favoured 4-5-1 formation after the 5-0 thrashing by Liverpool.
Sherwood went for a side and shape that was radically different to what had gone before. Out went most of the summer signings, to be replaced by a core of English players, many of whom Sherwood has worked with in the youth ranks. Danny Rose and Andros Townsend were restored, giving Spurs pace and width, with Aaron Lennon on the opposite flank.
With Sherwood urging his players to get the ball forward quickly, Spurs did just that, to the approval of their fans, who were relieved to see their team playing with attacking zest once again.
The trouble was the end product was not much better than it was under Villas-Boas. While there was an admirable directness about the home side’s play, they were sloppier in possession and lost their shape too easily.
When Mousa Dembele reverted to type by playing the ball back towards his defence from the centre circle, Sherwood was almost apoplectic with rage, jumping up and down on the touchline and swearing profusely.
He soon got the hang of touchline theatrics, berating the fourth official one minute, sharing a joke with Sam Allardyce the next.
But much as he, and a crowd rejuvenated by a change of manager and style, roared their team on, Tottenham struggled to find a way past West Ham’s stubborn defence. Adebayor headed wide and then shot high into the stands, Defoe shot wide and high, and Kyle Walker sent a free-kick dipping over the bar from 30 yards.
Then came the breakthrough, and a moment that vindicated the changes Sherwood had made. With West Ham enjoying a rare opportunity to attack, with a corner, Spurs broke quickly. Townsend ran half the length of the field before slipping the ball forward to Defoe. The England forward darted down the left touchline, looked up and floated a perfect pass for his partner, Adebayor, to smash a waist-high volley in off the underside of the bar.
The crowd erupted in delight, Sherwood danced on the touchline, and it looked like the perfect start to his managerial career.
But West Ham had other ideas. The team that had barely had a sniff of goal suddenly went looking for an equaliser and Hugo Lloris was called into action, saving well first from Mohamed Diame and then Matt Taylor.
The Hammers were not to be denied and Matt Jarvis equalised with 10 minutes to go, smashing in an angled shot after a classic route one build-up. And four minutes later they took the lead when Maiga headed in Diame’s cross at the far post. Suddenly Sherwood looked lost for ideas. Adebayor had been replaced minutes earlier by Lewis Holtby, leaving Defoe as the only striker, and try as they might, they could not find a way back.
Welcome to the mad world of football management, Tim.
TOTTENHAM: Lloris 7; Walker 7, Capoue 7, Chiriches 6, Rose 6 (Fryers 61); Lennon 6, Sigurdsson 6, Dembele 6, Townsend 7 (Chadli 72); Defoe 6, Adebayor 7 (Holtby 78)
WEST HAM: Adrian 6; McCartney 6, Rat 7, Collins 7, O’Brien 7; J Cole 6 (Diame 69), Taylor 6, Diarra 6 (Morrison 78), Collison 6, Jarvis 7; C Cole 6 (Maiga 64)
Referee: Neil Swarbrick