Tottenham have endured a miserable start to the Premier League season, picking up just one win from their opening seven outings, though performances have improved of late despite goals and wins being hard to come by.
Monday's win at home to Coventry was far from Spurs' finest performance, but a sensational strike from the returning James Maddison plus goals from Omar Marmoush and Ben Davies secured a first Premier League three points for De Zerbi's side.
However, Spurs face a much tougher test on Saturday evening as they travel to Stamford Bridge to take on Chelsea. Xabi Alonso's side sit fourth in the Premier League table and have won their last two games against AFC Bournemouth and Everton, though the concern for Spurs is more than just current form.
Tottenham have just one win in their last 34 league visits to Stamford Bridge, with Chelsea winning their last six games against their London rivals and unbeaten at home to Spurs since April 2018.
Tottenham's Last Stamford Bridge Win
The last time Tottenham tasted victory at Stamford Bridge, Mauricio Pochettino's side produced a memorable comeback to win 3-1 in April 2018.
Chelsea had taken an early lead through Alvaro Morata, but Christian Eriksen's brilliant long-range effort brought Spurs level before Dele Alli struck twice after the break to secure all three points.
That win ended a 28-year wait for a league win at Stamford Bridge for Spurs, who had last won there on 10 February 1990 with goals from David Howells and Gary Lineker, either side of John Bumstead equalising for Chelsea.
However, rather than the 2018 win becoming the start of a new chapter of success at Stamford Bridge, visits to Chelsea have continued to be disappointing for Spurs supporters since then.
A Torrid Recent Record
Tottenham have repeatedly struggled to get the better of Chelsea in recent seasons, especially on their own ground. Since their last win at Stamford Bridge, Spurs have beaten the Blues just four times in 21 meetings, and not once away from home.
There has been some respite for Spurs at Stamford Bridge, with a goalless draw in 2020 and a thrilling 2-2 draw in 2022, but Chelsea have emerged victorious in each of the last three meetings in west London by an aggregate score of 5-1.
Last season's meeting came in the final week of the season, with goals from Enzo Fernandez and Andrey Santos helping the Blues to a 2-1 win, despite Richarlison getting one back for Spurs 16 minutes from time.
These recent results show the task De Zerbi has on his hands if he is to end Tottenham's woes at Stamford Bridge.
Can Tottenham Break the Curse?
Spurs will take some inspiration from the win against Coventry and their positive performance away to Manchester United, though Chelsea present the toughest task of their season to date.
With injuries to the likes of Savio and Lucas Bergvall, as well as doubts over the fitness of Pedro Porro and Andy Robertson, who was forced off against Coventry, Spurs could be without some important players for the trip across the capital.
However, they have been boosted by the return of Maddison to the starting eleven and the long-awaited return of Dejan Kulusevski, both of whom are capable of producing a moment of magic that could prove decisive.
Keeping Chelsea's forward line quiet will be a challenge for De Zerbi's team, but Spurs fans will be desperately hoping they can put an end to the Stamford Bridge hoodoo and come away with a priceless three points.
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