Sherwood may have had a smile on his face with Spurs on the way to his 13th victory in 22 Premier League games in charge, earning sixth place in the table and a Europa League berth, but he was also probably aware by then that a new man would be in one of English football's hottest seats by next season.
It was finally confirmed on Tuesday that chairman Daniel Levy had implemented the break-clause in an 18-month contract that the former England international signed in December.
Statistically he was the most successful Tottenham manager in the Premier League era, averaging almost two points per game.
But ever since Harry Redknapp was sacked in 2012 after taking the club to fourth place for the second time in three years, bewildered fans have wondered what the key criteria are for a Spurs manager.
Reaching the Champions League appears to be a minimum requirement, despite fierce competition from some big spending rivals.
Tottenham have tended to sell leading players like Luka Modric and Gareth Bale (to Real Madrid) before investing.
Receiving more than 80 million pounds ($134.97 million) for Bale nine months ago enabled the club to spend heavily on transfers but although seven players were brought in, few have been successful.
SUPPORTERS AGHAST
Christian Eriksen, the talented Danish midfielder, was one of the only ones to impress supporters aghast at how little impact was made by expensive signings like Erik Lamela from AS Roma and Roberto Soldado from Valencia.
Andre Villas-Boas, the previous manager, hinted that technical director Franco Baldini was responsible for some of the deals.
Whoever wanted them, Villas-Boas understandably found it difficult to integrate so many new recruits unfamiliar with the pace and physicality of English football.
He paid with his job in December, when Sherwood's in-house promotion always seemed a temporary measure.
There was widespread surprise he was given an 18-month contract and media speculation was rife early on that he was merely keeping the seat warm for a more experienced manager.
If the plan was to install Netherlands coach Louis van Gaal after next month's World Cup in Brazil, it appears to have been scuppered by Manchester United's interest in the Dutchman.
Levy still seems set to continue the pattern of alternating English managers and foreign ones, having moved from Spaniard Juande Ramos to Londoner Redknapp, then Villas-Boas and Sherwood.
The bookmakers favourites are Southampton's Argentinian manager Mauricio Pochettino, who has the advantage of Premier League experience, and Van Gaal's fellow countryman Frank de Boer.
Whoever arrives as the ninth permanent manager in Levy's 13 years as chairman it will be a huge task to return Tottenham to the top four.
($1 = 0.5927 British Pounds)
(Editing by Tony Jimenez)
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