Richarlison snatched a dramatic stoppage-time winner as 10-man Tottenham Hotspur defeated London rivals Chelsea 2-1 in an entertaining pre-season friendly played before more than 80,000 fans at Stadium Australia in Sydney on Saturday.
Club-record signing Sandro Tonali also marked his first start for Spurs with his maiden goal, helping the North London side secure victory despite playing the entire second half with 10 men.
Tottenham took the lead in the 19th minute when Tonali latched onto Manor Solomon’s pass on the edge of the area and fired a shot that took a deflection before beating the goalkeeper.
Chelsea responded almost immediately, restoring parity two minutes later through Estevao, who headed home at the far post after Romeo Lavia surged through midfield to create the opportunity.
The game became increasingly physical after Conor Gallagher was booked for a heavy challenge on Dario Essugo in the 10th minute, sparking a brief confrontation between players from both teams.
Spurs suffered a major setback shortly after the restart when defender Kevin Danso was sent off just three minutes after coming on as a substitute.
The centre-back received a straight red card for bringing down Joao Pedro, leaving Tottenham to play the remainder of the contest with 10 men.
Chelsea seized control following the dismissal and created a series of chances, with Estevao striking the crossbar during a sustained spell of pressure.
However, the Blues failed to convert their numerical advantage into goals.
Their wastefulness proved costly in the closing moments as Richarlison latched onto a late opportunity and calmly side-footed home in the 90th minute to hand Spurs an unlikely victory.
The defeat handed new Chelsea manager Xabi Alonso his first loss since taking charge.
His side had opened their pre-season campaign with a thrilling 6-4 victory over Western Sydney Wanderers and will now travel to Hong Kong to face Juventus on Wednesday.
Alonso has overseen an active summer transfer window, highlighted by the signing of Morgan Rogers from Aston Villa, as he looks to revive Chelsea following last season’s disappointing 10th-place Premier League finish.
Tottenham, who narrowly avoided relegation after finishing 17th last season, have also strengthened their squad with the arrivals of Tonali, Matheus Fernandes and Andy Robertson.
Chelsea handed summer signing Marco Palestra his first appearance after his move from Atalanta, while Cole Palmer and Estevao returned to the starting lineup after missing the opening friendly.
Fernandes remained unavailable for Tottenham because of a calf issue, while James Maddison also missed the match with a minor injury.
Despite Chelsea dominating the second half with an extra player, Tottenham showed resilience and punished their rivals late on, ending their Australian tour with a memorable victory.
