After the sacking of Andre Villas-Boas in December, the former midfielder was thrust into the role as head coach and, after a successful temporary spell, penned an 18-month deal.
Sherwood has enjoyed a successful time in charge and boasts a better win percentage than any other Tottenham manager in the Premier League era, yet that does not appear to have been enough to win over chairman Daniel Levy and sections of the fan base.
As a result, the head coach - fresh from his nomination for April's manager of the month - leads his side into the final two matches staring down the barrel, with Sam Allardyce of Saturday's opponents West Ham facing a similarly-uncertain future.
Asked with hindsight if he would have done anything differently, Sherwood said: "No, I'd do it the same way. Like Sam has just told you, it's a results business.
"It's not me who makes the decisions. It's not up to me, it's up to the club to see how they want to move the club forward."
Regardless of results Sherwood has had to deal with questions about his future ever since taking the job, although this week has been more difficult than most.
Frank de Boer fuelled speculation by saying he was open to speaking with Tottenham about taking over as manager, with the Barclays Premier League club feeling the need to release a statement denying rumours they had contacted Ajax about him.
"I wasn't shocked at first because I just thought it was speculation," Sherwood said. "But when Ajax came out and said they were approached and Frank, then Tottenham coming out on top of that and say they weren't, then obviously it doesn't sit well."
Despite that, Sherwood has not sought private clarification, saying: "If the club felt it was necessary they would have come to me and told me."
Asked why he has not asked Levy what is going on, he said: "Because he would say, which he has said to me and I've told you previously: 'At the end of the season we will sit down and talk about it'.
"And if we win the next two then surely I've got to have a chance. But like I said earlier, it shouldn't be down to a couple of results."
However, reports suggest Levy has already made up his mind, so does Sherwood still have the same respect for those around and above him as when he took the job?
"Yeah, I've said it and I haven't changed my mind," he said. "Daniel Levy wants the best for this football club. Always does. I've always felt that about him.
"I don't know if he's misunderstood because I don't read what people are saying about him too often, but he really does want the best for the club.
"He will make a decision based on what he thinks or based on what people are talking to him think is the best move for the long-term future of the club.
"I do think the next move has to be the long-term future. It cannot be someone in and gone again. Without stability you're never going to achieve anything."