Roberto De Zerbi has five games to save Tottenham from the unthinkable nightmare of relegation from the Premier League after his first home game at the helm ended in a costly 2-2 draw against Brighton.
The London club took the lead through Pedro Porro but were pegged back by a Kaoru Mitoma wonder goal on the stroke of halftime.
Both teams had chances after the break but the impressive Xavi Simons put the home side back in front with a dazzling strike in the 77th minute as the stadium erupted.
Long-suffering Tottenham fans dared to believe their team could hold out for a first league win since December but their hopes were cruelly dashed deep into stoppage time when Georginio Rutter drilled home.
The draw left Spurs 18th in the Premier League, a point from safety.
West Ham, in 17th spot, and Nottingham Forest, one place higher, are both in action over the next two days.
Thousands of supporters at the Tottenham Hotspur Stadium waved flags ahead of kick-off, desperate to lift their team, and Spurs responded by making a bright start.
Despite the early pressure Brighton, chasing a European spot next season, went agonisingly close to taking the lead when Micky van de Ven kicked the ball onto the post with Danny Welbeck lurking.
But it was Tottenham who took the lead, when defender Porro beat flailing Brighton goalkeeper Bart Verbruggen to a Simons cross, nodding the ball into an open net.
The goal led to an enormous outpouring of relief from desperate fans, and Spurs now had their tails up.
Spurs should have doubled their lead just moments after the goal when Simons stroked the ball against a post after a fine attack down the left.
They were made to rue that missed opportunity when Brighton substitute Mitoma scored a dazzling equaliser in first-half stoppage time.
Pascal Gross swung in a long cross from the right which dropped to the Japanese winger, lingering unnoticed at the back post.
Mitoma watched the ball as it dropped and sweetly side-footed home a volley, sucking the energy out of the stadium.
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PRESSURE
Spurs came out in the second half knowing they faced a defining 45 minutes and both sides had chances to take the lead.
Simons appeared to have won the game for Tottenham with his moment of magic.
Brighton defender Jan Paul van Hecke lost the ball and Spurs substitute Lucas Bergvall found Simons on the left.
The midfielder cut inside and lashed home from the edge of the box, diving into the crowd to celebrate with delirious fans.
But Brighton were not finished, pouring forward in search of an equaliser.
They had their reward when substitute Rutter smashed Van Hecke's cutback into the top corner in the 95th minute, leaving Spurs players distraught.
Tottenham are facing an almost unthinkable relegation nearly half a century after they suffered a similar fate.
The club won the Europa League last season under Ange Postecoglou but dispensed with the Australian's services after finishing 17th in the league.
They signed former Brentford boss Thomas Frank but sacked the Dane in February, ushering in an ill-fated short stint for interim boss Igor Tudor.
Spurs are the ninth-wealthiest club in the world, according to Deloitte's latest rankings, underlining the extraordinary nature of their predicament