It seems that speculation has surrounded the Head Coach's position throughout the season.
Ever since the sacking of Andre Villas-Boas at White Hart Lane in December, there have been question marks over his replacement, even though he signed a deal until the end of next season.
Louis Van Gaal, Mauricio Pochettino and Frank De Boer have been those that have been linked the strongest to the hotseat at White Hart Lane, whilst former Liverpool and Chelsea boss Rafa Benitez has also been mentioned along with current Everton boss Roberto Martinez.
But during this time Sherwood has had to answer uncomfortable questions regarding his future. The only time that the club has made any sort of move is when they released a statement in light of claims that De Boer claimed he was approached to manage Spurs.
This season has seen the club miss out on Champions League football following a summer where several players came into the club after the departure of Gareth Bale for a world record fee. It was always going to be a difficult task for Sherwood to achieve the pre-season objective, as he was off the pace when he was handed the job. It looks as though Spurs will have to be content with Europa League football instead next season.
But to hand him a deal that goes into next season, and for stories to emerge that managers are being considered for next season can’t be good for both Sherwood, or any potential candidate for the role.
Some may not think Sherwood is good enough to be the man in charge at White Hart Lane, but it doesn't look good from the outside when you've got a man trying to do a job, whilst reports are circulating on a daily basis linking other figures to the role.
What does it if you're one of the candidates looking for work, knowing that the current boss is line to be replaced after only a very short time at the helm?
Former goalkeeper Paul Robinson described it as a 'PR disaster'. Some will agree that if you’re only planning to give a man until the end of the season, then you should only give him a deal up until then, instead of giving him the next season and then turn around and decide that you want to replace them.
It just seems very complicated at White Hart Lane at the moment. The part they seemed to have fallen down is offering Sherwood a deal beyond the end of this season, otherwise this situation would seem very different, and maybe less complicated. Maybe that was the biggest mistake made by the club's hierachy.