An initial positive spell after succeeding Andre Villas-Boas has long been forgotten, with the former Spurs midfielder's position coming under increasing scrutiny.
Sherwood appears to be facing a fight to keep his job this summer, with chairman Daniel Levy frequently reported to be looking for a new man to fill the White Hart Lane hot seat.
That would be a welcome development for a number of Tottenham fans, whose scepticism about their head coach has only grown in recent weeks.
A number of supporters expressed their irritation at Sherwood watching from the stands in last weekend's mauling at Liverpool. And while he will be in the dugout when Sunderland visit on Monday, Sherwood promises he will make no compromises.
"You are damned if you do and damned if you don't," he said. "If Jose Mourinho sits up there (in the stands), he's fine.
"Nigel Pearson at Leicester has sat up there all season. But I am realistic to know it's Tottenham, you are under the spotlight no matter what you do.
"You've got a rookie manager coming in here, won the first eight games or whatever it was and everyone thinks it's easy. I didn't, I was realistic, I knew there were going to be some downs.
"It was a case of just cracking on. But whatever decisions I make are my decisions. If I'm going to go down, I'll go down my way."
That last comment made Sherwood sound as if his fate was sealed - that, though, was something he was quick to deny.
"No, I am talking about this season before we start planning for next year," he said.
"It's just one stage at a time and I've got six cup finals between now and the end of the season, and it's really important to me that we show the fans something to make them optimistic about next season."
Sherwood wants to see some fight from his players in Monday's match against Sunderland, but not the type he was rumoured to have been involved in at Anfield.
There was much speculation after the match that the Spurs head coach had punched a player in the dressing room, with the rumour gaining so much momentum that even his family got het up.
"It was incredible the way that it gathered so much pace," Sherwood said, joking about the unfounded speculation.
"I was getting family and friends texting me saying, 'Why did you do it?'. They didn't say, 'Did you?', it was all 'Who did you hit?'."
The rumour fuelled the narrative that Spurs is in chaos right now but Sherwood had nothing but praise for his players, some of whom took to social media to hit out at talk of a dressing-room fight.
"Did they?" Sherwood said of players like Aaron Lennon and Roberto Soldado defending him. "I don't know because I'm not on Twitter - that's why I don't speak with Gary Lineker.
"I didn't know if the players had come out or not, I hadn't heard that but I am not surprised. They know I want the best for the club.
"And that helps them out because it means I want the best for them, but I am not going to suffer fools. That is the way I manage."