Talking ahead of Monday's game with Sunderland, the Tottenham boss has clearly forgotten victories at Manchester United, Liverpool, Arsenal and Manchester City last year.
In a press conference this week, Sherwood fielded questions from journalists regarding a number of matters that have emerged.
Talking about last weekend's crushing defeat to Liverpool, and of reports of dressing room issues that may be affecting the player's motivation, the ex-Blackburn man moved to reassure fans.
"The atmosphere has been good in the dressing room," Sherwood said ahead of Monday's game with Sunderland.
"They shouldn't need anyone to motivate them, I never needed motivating to play football," the Spurs boss reasoned. "If you need motivating then you shouldn't be in this game. You've got 35,000 fans coming to cheer you on, if you need someone to motivate you you shouldn't be in this game."
It is not the first time Sherwood has compared his own experience of being a professional footballer to those he is responsible for now as Tottenham manager. What is a concern is that despite his attempts to appeal to the common sense of many from his era of professional football, it may not be something that resonates with the Spurs squad today.
Moving on to talk about the club's poor results against the top teams this year, Sherwood went on the defensive somewhat, saying: "It's not a new thing, if you look at history, Tottenham don't beat the top teams. And they haven't done for many many years.
"To play against Sunderland and to play against Liverpool, it's still only three points as much as they're high profile games and we want to win them.
"We're still smartly positioned in the league despite not winning those games. We're still smartly positioned in the league despite not winning those games, it certainly needs to be addressed if we want to step up."
Sherwood's efforts to play down the high profile defeats don't seem to take into account the fact that last year Spurs beat three out of four of the top four (Manchester United, Manchester City and Arsenal), as well as this year's league leaders Liverpool. It also crucially doesn't explain the fact that Tottenham haven't just lost those games this year, they've been trounced in many of them.