The former Spurs midfielder is reportedly set to be replaced this summer.
Despite a commanding 5-1 win over Sunderland on Monday night, Tottenham are looking decidedly likely to miss out on Champions League qualification again this season.
The North London club replaced Andre Villas-Boas with Tim Sherwood mid-season and the rumours are starting to fly that there will be another change in manager at the end of the campaign.
The lack of longevity at White Hart Lane since Daniel Levy’s introduction to the club is slightly worrying, and is not dissimilar to the practices of another London outfit.
Sherwood’s reign at Tottenham has a striking resemblance to Roberto Di Matteo’s time at Chelsea, with both struggling to live up to expectations and simply not having a big enough reputation to please their masters.
Despite winning the Champions League for the west London outfit, the Italian boss was shown the door in a disgraceful lack of faith by Roman Abramovich.
Although Sherwood’s achievements are nowhere near what Di Matteo accomplished, both were constantly undermined with the appeal of bigger-name replacements in mind.
For Chelsea, the chance that Pep Guardiola could be tempted out of a sabbatical was reason enough to give Di Matteo his marching orders.
At Tottenham, the hint that Louis van Gaal could move to Spurs after the World Cup is seemingly good enough to dispense with a former player but inexperienced manager.
Just what Di Matteo could have achieved at Chelsea will never be known, but he clearly showed ability to become a world-class manager.
For Sherwood, given time he could well be the man to steer Spurs back into the Champions League. However, due to the high-pressure environment of Premier League football, he is likely to be replaced by someone more senior.