Tottenham Hotspur's crisis deepened on Friday (AEDT) as Micky van de Ven was sent off and the hosts slumped to a 3-1 loss to Crystal Palace in north London.
Relegation is now a distinct possibility for the beleaguered club, who sacked manager Thomas Frank in February after just eight months in charge.
His replacement, former Croatia defender Igor Tudor, now has a huge job on his hands after many furious fans left the stadium at halftime with Spurs in a 3-1 hole.
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Spurs are 16th on the ladder and just one point ahead of Nottingham Forest and West Ham United, the latter of which is in the third relegation position.
The last time Spurs dropped out of the top division was back in 1977.
It all started so promisingly, when striker Dominic Solanke gave the home side the lead in the 34th minute.
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But the match defining moment came four minutes later when world class centre back Micky van de Ven was sent off for dragging down Palace winger Ismaila Sarr in the box.
Sarr then converted the penalty before Palace struck twice more in an extraordinary passage of first half added time.
Jorgen Strand Larsen gave the visitors the lead before Sarr helped himself to a double seven minutes into added time.
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Spurs sacked Australian manager Ange Postecoglou after he won the Europa League last season.
Postecoglou paid the price for finishing 17th in the league last season.
Spurs are the only team that hasn't won a league game in 2026.
They have lost seven games and drawn four.
Only in 1935 (first 15 games) have Tottenham endured a longer winless run in league football to begin a calendar year.
There are nine games left in the league season.
"It's hard to find any positives for Spurs. In weeks," commentator Steve Wilson said on Stan Sport's coverage.
"Spurs have had some pretty bad days this season but this is right up there. A terrible evening."
Palace fans taunted Spurs by singing "Say hello to (Championship club) Millwall."
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Tudor described the match as "two games."
"After the red card, it was a different game. The second half, we tried," he said.
"I saw interesting things second half. Very disappointed, like the fans. We need to stay quiet, keep working and believe. After this game, I believe more. Maybe it sounds strange, but I saw something in the team. Even now in the dressing room after the game. Some energy, some passion, the fight. It was there.
"Unfortunately the red card changed the game, but there are still nine games to play. We need to stop talking about pressure. This is not a topic to speak about. I will not speak any more about pressure."
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