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A horror moment for Manchester United veteran Jonny Evans gifted the Community Shield to Manchester City after a penalty shoot-out.
Evans lifted his spot-kick over the crossbar before Manuel Akanji tucked in the winning penalty as Pep Guardiola’s side secured the first silverware of the season.
Alejandro Garnacho thought he had inflicted more Wembley misery on the four-time Premier League winners when he repeated his FA Cup final goalscoring heroics from just 77 days earlier with nine minutes remaining.
But another substitute Bernardo Silva, headed a last-minute equaliser for City to make it 1-1 and take the match to spot-kicks.
Andre Onana saved from Silva early in the shoot-out but Jadon Sancho, back for United following his bust-up with Erik Ten Hag, saw his kept out by Ederson.
Evans then blazed United’s eighth penalty high over the top before Akanji secured a 7-6 win for City.
City were without their contingent of Euro 2024 finalists with England trio Phil Foden, Kyle Walker and John Stones rested as well as triumphant Spain midfielder Rodri.
But despite whatever the relative merits of this annual curtain-raiser are, Guardiola certainly seemed to be taking this one seriously when he gesticulated furiously at his coaching staff before storming down the tunnel at half-time.
Jack Grealish was a surprise absentee while Kevin De Bruyne and Silva started on the bench.
So it was left to their supporting cast to provide the early fireworks and Jeremy Doku was the first to show any attacking intent, nutmegging Diogo Dalot down the left before fizzing in a low cross just behind debutant Nico O’Reilly.
Oscar Bobb then fed James McAtee, who came closer still when he curled his shot around Onana and back off the inside of the far post.
United, with Mason Mount and Bruno Fernandes the furthest forward and Marcus Rashford playing on the left wing, created their first chance just before the half-hour when Amad Diallo curled a shot across goal and wide.
And it was Ten Hag’s side who should have scored moments later when Diallo played a one-two with Casemiro and squared the ball for Mount, who was just too slow to react for what would have been a tap-in.
Rashford, who, like Grealish, was left out of England’s squad in Germany, had an early chance to impress the watching interim national boss Lee Carsley when Casemiro found him unmarked on the left, but he stabbed his shot tamely across goal and wide.
United thought they had taken the lead eight minutes into the second half when Lisandro Martinez played in Fernandes, who curled a superb effort over Ederson and into the net, but the Portugal star was flagged offside.
A raft of substitutes for both sides followed, including debuts for young United midfielder Toby Collyer and City’s £30million summer signing, the Brazilian winger Savinho.
Then came a big moment for Rashford, Garnacho squaring the ball to leave the forward clean through, 14 yards out, unmarked and with just Ederson to beat – only for a hurried, first-time effort with his left foot to clip the post.
A United goal was coming, though, and it arrived nine minutes from time when Fernandes swept the ball across goal and Garnacho expertly applied the finish.
But with just a minute to go City hit back, Bobb swinging in a cross and Bernardo Silva rising above Facundo Pellestri to nod home the equaliser and take the encounter to spot-kicks.