Tottenham won at Stamford Bridge for only the second time in the league for 36 years as 10-man Chelsea were beaten at home.
England midfielder Cole Palmer was also sent off in the 80th minute for two bookings to complete a miserable evening for Xabi Alonso’s side.
Spurs had taken the lead three minutes earlier in fortunate circumstances.
Chelsea goalkeeper Mike Penders, on his first league start for the Blues after Emi Martinez suffered a fractured jaw against Everton, punched the ball into his own net when he jumped under pressure from Jan Paul van Hecke at a corner.
French forward Mathys Tel added a second in the 87th minute with a low strike from 25 yards out following a fine individual run from the halfway line.
The match was played in torrential rain and it was stormy on the pitch too in a fiery derby encounter.
Palmer picked up his two bookings in a nine-minute spell, either side of Tottenham’s opener.
His first yellow card came when he barged into Mateus Fernandes, with the second following a late challenge on Conor Gallagher.
Spurs moved up to 12th place, having won two matches in a week after they gained their first league victory of the campaign on Monday with a 3-1 home win over Coventry City.
As much as it was deserved, it was unexpected given their wretched record at the home of their London rivals.
Tottenham had won just one of their last 36 league visits to Stamford Bridge with 11 draws and 24 losses. The only previous victory in that run had come on 1 April, 2018 when Mauricio Pochettino’s Spurs won 3-1 against a Chelsea side managed by Antonio Conte.
Before that, you had to go back to 10 February, 1990, in the old Division One when a Spurs team led by Terry Venables won 2-1 at Stamford Bridge against Bobby Campbell’s Chelsea side.
Chelsea analysis: Blues struggle after Penders error
It was a troubled night for Alonso’s side, who lost at home in the league for the first time this season.
The Blues, who would have moved level on points with third-placed Brighton had they won, created the better chances when the game was goalless but visiting goalkeeper Antonin Kinsky saved well from Palmer, Jordan Henderson and Pedro Neto.
Chelsea handed 21-year-old Penders his opportunity in the absence of Martinez and he did well to keep out Omar Marmoush’s side-footed effort from Andy Robertson’s left-wing cross and also denied Tel.
But the Belgian was to blame for the crucial opener, and may feel he should have also done better with Tottenham’s second goal.
Chelsea missed injured striker Joao Pedro, with Morgan Rogers ineffective in a false nine role, while 19-year winger Geovany Quenda also struggled to have an impact as he started a league game for the first time since a £40m summer move from Sporting.
Boss Alonso will also have to make do without Palmer for Wednesday’s Carabao Cup last-16 tie at Anfield against Liverpool after the forward’s first career red card.
Tottenham analysis: Spurs show quality, but another Maddison injury blow
For Tottenham, their position of 12th is their best in the top flight since a goalless draw at Brentford left them in that spot at the beginning of January.
Fans who saw their team win the Europa League in 2025 will still expect more, but back-to-back victories will provide encouragement and hope.
Spurs only stayed up on the final day of last season and were the last top-flight team to win a match in this campaign.
But Roberto de Zerbi’s men showed they have the quality to rise up the table, with 68.5% of possession and 15 shots, compared to only seven from Chelsea, although both sides had four attempts on target each.
The only negative was another setback for midfielder James Maddison.
After a serious knee injury, he made his first start for Tottenham since May 2025 against Coventry on Monday, scoring in the crucial success against his former club.
However, after impressing in the first half at Stamford Bridge, Maddison only lasted five minutes of the second before he dejectedly walked off slowly with another problem.
Supporters will hope it is nothing serious, with Spurs having another London derby, at home to Crystal Palace, next Saturday.
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