Before he took on the job, 45-year-old Sherwood had plenty of admirers in the football community. His passion for the game was clear to see and his leadership qualities were well-known; he had guided Blackburn Rovers to their first and only Premier League title back in 1995 as captain.
And his long-standing association with the club who call White Hart Lane home, as a coach for five years, meant that he had a connection with the team and would likely better identify with their long-term goals and plans than many of the other candidates back in December.
Now it seems the former England international can do no right as Tottenham have cut an increasingly direction-less and weak figure on matchday.
What started as an encouraging foray into management at the highest level, with a six-match unbeaten run in the league, has since developed into a farcical implosion.
Since the end of January, Sherwood's side have lost heavily against City, Liverpool and Chelsea, while they also went down against the Gunners to a score-line of 1-0.
In truth, it's been their complete deficiency in experience challenging the league's top four that has really put a sizeable dent in their confidence. And while it would be unfair to place the blame solely at Sherwood's feet, he's certainly played his part; he wasn't proactive enough with his tactics and decision-making in stopping Liverpool's danger from the flanks when they travelled to Anfield, for example.
And he hasn't extracted the best from the huge pool of talent he has at his disposal. The likes of Paulinho and Roberto Soldado continue to underwhelm without any real readjustment on the cards from the sidelines.
Nonetheless, for all his flaws and inexperience, the Spurs supremo can still demand his players to make one last push for their final flurry of games, and he can still have a positive effect on the club even if he gets the sack come the summer—pretty much all of their remaining matches are winnable.
Make no mistake, like any club inside the top half of the table, Spurs need to avoid stagnating—and Sherwood needs to guarantee that doesn't happen.