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Tottenham drew 2-2 with Brighton, extending their winless streak to five games. The club is now at risk of relegation for the first time in nearly 50 years.
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With each winless game that passes, a once unthinkable fate for Tottenham becomes increasingly likely.
The facts are that Spurs now stand five games away from a first season in the second tier for almost 50 years, and one match from equalling the club's worst-ever winless league run, set in 1935.
Yet, while it may not feel it in the immediate aftermath of Saturday's cruel setback, there were signs of encouragement for De Zerbi, who has insisted first and foremost on restoring confidence in his players to aid their survival bid.
A team sheet featuring midfielder Rodrigo Bentancur, making his first start since undergoing hamstring surgery in January, and James Maddison, returning to the squad after tearing his anterior cruciate ligament in pre-season, already provided a pre-match lift.
The Spurs fans waved flags bearing the club's crest before kick-off and roared as the stadium announcer read out the player's names as they sought to create an atmosphere in which their confidence-stricken team could thrive.
The hosts carried the greater early threat and had a penalty claim dismissed when Destiny Udogie went down after getting past Yankuba Minteh.
They went close to a quick-fire second after Pedro Porro's opener when the excellent Simons' struck the post, and Bart Verbruggen saved Porro's follow-up.
There were uncomfortable moments as Brighton began to threaten, but Spurs showed great resolve to force the breakthrough, while provided a touch of class as the stadium became increasingly nervous in the second half.
Tottenham is currently on a five-game winless streak in the league.
Tottenham is five games away from potentially facing relegation for the first time in almost 50 years.
Tottenham's worst-ever winless league run was set in 1935, and they are one match away from equaling that record.

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Ultimately, De Zerbi's men could not withstand Brighton's late pressure - but the Italian will hope this performance can inspire his side with time quickly running out.