In 1984, Keith Burkinshaw was still at the helm of their bid to win the Uefa Cup. But he had grown so disillusioned that by the April of that year, he was gone. His resignation was on the table and he would only linger on to ensure he won the trophy the following month, which he did over two hard-fought legs against Anderlecht.
So often this season, it has looked to outsiders as though Spurs were once again on the hunt for a new boss. For months, Ange Postecoglou has seemingly had one foot out the door, awaiting a final push from Daniel Levy that has not come. The Australian may yet repay that faith by winning the Europa League to whitewash a miserable, torrid season.
After the smash-and-grab in Frankfurt that edged them into the last four of the competition, he took perhaps the greatest pleasure from the manner in which his players had shut out the noise.
"A fightback in Frankfurt that will go down in folklore!"
It's huge celebrations from the Tottenham players and staff as they book their semi-final spot in the Europa League
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The path to Bilbao has opened up tantalisingly, with Bodo/Glimt lying in wait next. It would, in many ways, be an absurdity for either Spurs or Manchester United to reach the final, let alone both, but suddenly it is entirely feasible.
It is not only that no coach since Juande Ramos has won a trophy with Spurs in the last 17 years. Postecoglou has had to navigate a furious injury crisis that at one point robbed him of 10 senior players. The core principles on which his project is based have been repeatedly trashed.
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Terry Venables, likewise, remains the last Tottenham manager to lift the FA Cup. But by that final of 1991, when they overcame Nottingham Forest at the Old Wembley, Spurs had only scraped into the top half of Division One on goal difference.
Football is of course, by nature, much more cutthroat and transitional than it ever was under any of those managers. Few know that better than Levy. Ramos beat Chelsea in the February; he was sacked in October 2008. Even Mauricio Pochettino was out of a job less than six months after the 2019 Champions League final.
The question which will dictate whether Postecoglou joins that pantheon is this: does he have the squad to win the Europa League, and if so why have they played as they have all season? If he does not, are they capable of doing just enough? Even at Tottenham, stranger things have happened.
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