Chelsea suffered its first defeat under Xabi Alonso after 10-man Tottenham Hotspur scored a 90th-minute winner to claim a 2-1 victory in a spirited pre-season friendly at Stadium Australia.
Sandro Tonali, the club record signing, opened the scoring for Spurs on 19 minutes when a strike on the edge of the box took a deflection to give Tottenham the lead. Chelsea responded almost immediately, Estevao heading home at the far post two minutes later after Romeo Lavia created space from midfield, and the teams went into the interval level.
The match tilted dramatically early in the second half. Kevin Danso, who had come off the bench at the break, received a straight red card three minutes after his introduction for a challenge on Joao Pedro. Chelsea dominated the remainder of the half with an extra player, testing the woodwork and piling on chances, including an effort from Estevao that hit the crossbar.
Despite enjoying long spells of control, Chelsea could not convert those openings, and Spurs capitalised at the death when Richarlison side-footed home in the 90th minute to snatch victory in front of 80,363 spectators.
The scoreline leaves Alonso preparing to travel to Hong Kong for a clash with Juventus on Wednesday carrying the first loss of his short tenure, following Chelsea's 6-4 win over Western Sydney Wanderers last week. The Spaniard has already overseen several high-profile additions as he reshapes a squad that finished 10th in the Premier League last season.
Tottenham, who narrowly avoided relegation after finishing 17th, have also been active in the transfer market, signing Matheus Fernandes from West Ham and Tonali from Newcastle. Tonali made his first start alongside fellow recruit Andy Robertson, while Matheus Fernandes missed the Sydney match with "fatigue in his calf muscle," and James Maddison was absent with a "small problem." Right-back Marco Palestra, a signing from Atalanta, logged his first minutes for Chelsea, and Cole Palmer started.
The result capped a short Australasian tour for Spurs that included a 2-0 win over Auckland FC and a 1-1 draw with Sydney FC. For both clubs the match will serve as a sharper test of match fitness and cohesion as the new season approaches, with Chelsea obliged to turn attacking dominance into goals and Tottenham buoyed by a late, dramatic finish.
