Arsenal came from behind to upset treble winners Manchester City on penalties following a 1-1 draw in the FA Community Shield at Wembley on Sunday.
City substitute Cole Palmer's 77th-minute goal looked to have secured yet more silverware for Pep Guardiola's side, but another replacement, Arsenal's Leandro Trossard, levelled the scores with a deflected shot deep into stoppage time.
The Gunners were perfect from the spot in the shoot-out, with Martin Odegaard, Trossard, Bukayo Saka and Fabio Vieira all on target, while City's Kevin de Bruyne fired his kick against the crossbar before Aaaron Ramsdale thwarted Rodri.
The Arsenal goalkeeper was quick to claim a psychological blow had been struck ahead of the start of the new Premier League season.
"For us, it's a statement," said Ramsdale. "It's a marker to know we can go and beat Man City in a big game when it matters. I'm not sure what it'll be like this season. But that mental block is gone. We're ready to push on now."
The victory earned Arsenal's club record signing Declan Rice – a £105m recruit from West Ham – his first piece of silverware for the club and he insisted it would be the first of many.
"I am buzzing, this is what I envisioned when I joined," said Rice. "City gave us what we expected. You have to have patience against them, you have to have mini games within the game against them like the manager said to us before.
"To win today, my first for the club. I feel I've grown a lot in the last three weeks. There's a lot of information to take in of what the manager wants. I'm eager to learn and keep improving. I'm sure we can achieve anything this season – we just need to remain focused."
The game was City's first competitive outing since June 10 and their historic treble-clinching Champions League final victory over Inter Milan.
After just three matches in pre-season, Guardiola had warned his team could be a little undercooked heading into this clash against an Arsenal side that had proved their closest challengers in last season's title race.
The Gunners ran out of steam down the stretch last term, and as if to demonstrate the freshly enhanced options at his disposal, coach Mikel Arteta handed debuts to all three of his major summer recruits.
Rice was pitched straight into the heart of midfield, while Kai Havertz, a £65m acquisition from Chelsea, led the line in the absence of the injured Gabriel Jesus. At the back, the versatile Jurrien Timber, a Netherlands international lured from Ajax, started at left-back.
For City, nine of the team that started at Wembley in June's FA Cup final were retained, with new signing Mateo Kovacic replacing the departed Ilkay Gundogan in midfield and Julian Alvarez selected ahead of the injury-hampered and benched De Bruyne.
While City had the bulk of the possession in the first half, Arsenal had the better chances, with Havertz twice spurning opportunities to bag a debut goal as he had two efforts saved by Stefan Ortega.
Guardiola's side showed more intent in the second half, with John Stones having a header saved, but it was substitute Palmer who broke the deadlock with a curling effort from the edge of the box which left Ramsdale with no chance.
Ramsdale was then called into action twice in quick succession, making saves from Phil Foden and Rodri to keep the deficit to one goal, with Arsenal digging deep to level the game via a deflected Trossard goal in the 11th minute of added time.
And the Gunners were rewarded for their resilience in the shootout as they picked up the first silverware of the new season and left City wondering how the game had gotten away from them.