Tottenham Hotspur fell to yet another defeat this season under Roberto De Zerbi as they crashed out of the EFL Cup at Anfield against Liverpool.
Spurs had opportunities to take the lead during the game, but went behind to a fine Alexis Mac Allister strike from the edge of the box in the first-half, before a stunner from Cody Gakpo in the second half doubled their lead. Conor Gallagher scored a header to pull one back, but they couldn't fight back to save themselves, with Dominik Szoboszlai scoring a screamer in injury time to seal a 3-1 win.
The result means that De Zerbi has yet to win a game this season against Premier League opposition, with the club's only victory coming against Championship side Charlton in round two of this competition, where they won 5-1. But they have lost against Brentford and Newcastle in the league, while also being held to 0-0 draws by Nottingham Forest and Everton.
De Zerbi was brought in at the back end of last season to save the club from relegation, and while he succeeded by the skin of his teeth thanks to a 1-0 win on the final day of the campaign, they have barely kicked on under his management.
The Italian was given full control of transfers and footballing decisions during the summer, spending almost £400m on ten new signings while also allowing for a number of top young players such as Luka Vuskovic, Will Lankshear, Tynan Thompson, and Pape Matar Sarr to move on permanently.
But despite those decisions and that power, he isn't delivering his end of the deal, and Spurs look set to be on course for yet another horror season.
De Zerbi was the club's top target for the role, and when they convinced him to come to North London they handed him a long-term five-year deal as part of the package to make him one of the highest-paid coaches in the country.
But at what point do they need to consider cutting their losses? When does too soon become too late?
Something Must Change or De Zerbi Could Go
Tottenham are clearly backing De Zerbi to succeed, and they have given him all the tools he needs to turn things around. The club broke their transfer record twice, have obliterated their wage structure, and given him full power.
But the team are wide open defensively, can't hit a barn door with a banjo themselves, and they are crying out for something to change so they can get back on track.
The manager will not change his ways, and he has been known to have a big meltdown and walk out if things don't go his way. Spurs have to be careful to avoid that situation, but they also need to ensure that they look after their own interests first.
If De Zerbi can't do that, then Spurs need to find someone who can, and they simply cannot afford to keep waiting until things get worse this time around. They need to be ruthless and make a decision at some point, and that time could be sooner rather than later.