Brazil striker Richarlison scored a 90th-minute winner and club record signing Sandro Tonali got his first goal as 10-man Tottenham beat London rivals Chelsea 2-1 in a feisty pre-season friendly in Sydney on Saturday.
Both sides fielded strong line-ups and Spurs struck first on 19 minutes through Tonali's deflected shot before Estevao levelled the scores barely two minutes later.
Tottenham defender Kevin Danso was given a straight red card just three minutes after coming off the bench at the break for bringing down Joao Pedro, with Chelsea dominating second-half proceedings.
But in front of 80,363 fans at Stadium Australia, they failed to capitalise and Spurs stunned them with a late winner.
"Very happy, especially for the first half because we played very well," said Spurs manager Roberto De Zerbi.
"The red card was no good for us, but also (not) for Chelsea because with the condition of the pitch, all players behind the line of the ball, it was tough for them.
"But we won a good game, a good test."
The loss means new Chelsea manager Xabi Alonso will head to Hong Kong for a clash with Juventus on Wednesday on the back of his first defeat, following a 6-4 victory over Western Sydney Wanderers in midweek.
"It was a really competitive game," said Alonso.
"The second half was really tight, after the red card we had a few very good chances to score.
"We missed them and at the end, very silly to concede that late goal, but I think that has been a good test for everyone."
The Spaniard has overseen a string of high-profile signings since being appointed, headlined by Morgan Rogers from Aston Villa, as he bids to rejuvenate the club after their disappointing 10th in the Premier League last season.
Players missing
Spurs, who fared even worse, coming 17th to narrowly miss relegation, have also been on a spending spree with Matheus Fernandes arriving from West Ham and Tonali from Newcastle.
They fly home after a 2-0 win over Auckland FC and 1-1 draw with Sydney FC.
Most of Chelsea's close-season signings have yet to link up with the squad, including Rogers.
But right-back Marco Palestra, who joined from Atalanta, got his first minutes while Cole Palmer and Estevao started.
Tottenham midfielder Fernandes, who missed the Sydney game with "fatigue in his calf muscle", was again absent, as was James Maddison with a "small problem".
But Tonali made his maiden start along with fellow new recruit Andy Robertson.
After a cagey start, tempers flared when Conor Gallagher hacked down Chelsea's Dario Essugo in the 10th minute with players pushing and shoving each other.
Gallagher was shown a yellow card and Essugo continued.
Spurs broke the deadlock after a nice break down the right from Manor Solomon, who fed Tonali on the edge of the box with his shot taking a deflection.
But it was a short-lived lead as Estevao headed home at the far post after Romeo Lavia broke free from midfield and they went to the break at 1-1.
Danso's brain-fade allowed Chelsea to dominate the second-half with Estevao rattling the crossbar among a slew of chances.
But, in a worry for Alonso, they failed to make the most of the extra man and Spurs stole their thunder when Richarlison side-footed home at the death.
