This has been an anti-climactic season at White Hart Lane, with the expectation brought by a flurry of summer signings quickly dampened.
Andre Villas-Boas' inability to adapt to life without Gareth Bale cost him the Spurs job in December, leading to Sherwood's appointment on an 18-month deal after an impressive spell in caretaker charge.
Things have not fared quite so well since, however, and the former midfielder is widely-expected to be replaced after the final four matches of the season.
First up is the arrival of embattled Fulham at White Hart Lane on Saturday - a match Sherwood approaches admitting he still does not know Spurs' best line-up.
"I couldn't tell you," he said. "And I don't know whether that's good or bad.
"I have assessed the players more than anyone. I could not tell you the best 11 players at Tottenham.
"They're are all so similar, much of a muchness regarding the same quality. I'm not sure there's any hierarchy or whether a player is like this good and that one is [that good].
"Our two exceptions are the goalie (Hugo Lloris) and Emmanuel Adebayor. Christian Eriksen is getting that way inclined, you can't leave him out at the moment."
The failure of Spurs' summer signings - with the exception of Eriksen - to hit the ground running have played a major part in Sherwood's inability to properly assess the squad.
Roberto Soldado, Erik Lamela and Etienne Capoue have struggled in their first season, while Vlad Chiriches, Paulinho and Nacer Chadli have only shown flashes of quality.
"All of them will benefit from a year here," Sherwood said. "All of them will be better, without a doubt, because they will have had a season in the Premier League.
"That's the ones who have played. You need to have a certain amount of games.
"Probably Erik and Etienne have not played enough but they will have benefited from a year in London and their language will be better and hopefully they can settle on the pitch.
"But the rest of them will all be better. All can improve."
Soldado, Lamela and Capoue will be sidelined again for the visit of Fulham, while injury also rules out Michael Dawson, Jan Vertonghen and Kyle Walker.
The latter has not featured for Spurs since March 13 due to a pelvic injury, but Sherwood does not think that will mean the 23-year-old will miss out on England's World Cup squad.
"I was hoping to see him on the training field at some stage but I don't' think he is ready," he said.
"What it is now there is a long time before the World Cup, they seem to have a lot of friendlies before so I am not sure that it is that important to their international manager if they played in the Premier League before that.
"It all depends on what options Roy has got at right-back. Glen Johnson is the only other option apart from Kyle Walker. Carl Jenkinson is not playing either and he is not injured."
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