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Xabi Alonso suffered his first loss as Chelsea head coach as the Blues were beaten 2–1 by Tottenham Hotspur in Sydney on Saturday.
Chelsea dominated the opening quarter-hour but still found themselves trailing 1–0 when a deflected effort from Sandro Tonali looped past a helpless Teddy Sharman-Lowe in goal, before Estêvão levelled with a well-taken header.
Spurs had begun to find their footing by the break, but the game swung back in Chelsea's favour just three minutes into the second half when Spurs centre-back Kevin Danso, introduced only at half-time, brought down João Pedro to deny a clear goalscoring chance and was immediately dismissed with a straight red card.
The sending-off altered the game's rhythm as Chelsea struggled to carve out clear openings against a resolute Spurs defence, and they were nearly made to pay late on when Rio Kyerematen rattled the crossbar on the break.
Just when it appeared the match was heading for a penalty shootout, Richarlison was left with a simple finish in stoppage time after Jamie Donley's shot rebounded off the post and fell perfectly to the Brazilian, securing Spurs' victory and handing Chelsea their first defeat of the summer.
'Battle of the Bridge' Heads Down Under
This was a friendly in name only.
From the very first whistle, the intensity of this rivalry was plain to see. Tottenham came out with an edge in the early stages, with Jan Paul van Hecke rekindling a feud with former Brighton & Hove Albion teammate João Pedro, while Conor Gallagher threw himself into a robust challenge after 10 minutes that earned him a booking.
Chelsea's competitive streak was perhaps less visible but certainly present, with both squads clearly eager to gain an edge over their rivals ahead of the new campaign. If either new manager had any doubts about the depth of this rivalry, those doubts will have been firmly put to rest.
Gittens's Hot Preseason Continues
Pedro grabbed the spotlight in the thrilling 6–4 victory over Western Sydney Wanderers, but winger Jamie Gittens, who has plenty to prove, is making a strong case for being Chelsea's standout performer of the summer.
Gittens netted in both closed-doors friendlies against Bromley and Crawley Town, then followed that up with a goal against Western Sydney before contributing an assist for Estêvão's equaliser here with a superb cross.
Few players are in greater need of a confidence-building preseason than Gittens, whose first campaign at the club failed to live up to expectations. With new arrival Morgan Rogers still recovering from World Cup duty, Gittens must make the most of every opportunity this summer. Thankfully for him, he's doing precisely that.
Familiar Problems for Chelsea
Danso's red card fundamentally shifted the dynamic of this match, as Chelsea were tasked with breaking down a Spurs side fully aware they had become the underdogs.
It's precisely the kind of scenario Chelsea encountered repeatedly last season, and the outcome was no different here. The Blues pressed and pressed, yet simply could not find a way through. Ultimately, their wastefulness in front of goal cost them, even if a flurry of late substitutions disrupted the flow of the game just as much as the red card had.
Alonso has now had his first encounter with this recurring problem, and with any luck, it gives him ample time to find a remedy before the season kicks off in earnest — when a defeat to Spurs would carry far greater consequences.