The Wembley curse is hanging dangerously for a third year running with Antonio Conte fearing he could become the latest victim.
The last two managers - Claudio Ranieri and Jose Mourinho - to win the title were both sacked midway through the following season after also losing the Community Shield.
Conte has already warned of a “Mourinho season” and the danger signs were there for all to see as Chelsea lost on penalties and looked a long way from the champions who won the Premier League with such style last May.
From being rock solid and untouchable last season, Chelsea are suddenly vulnerable, the doubts and question marks are mounting with the campaign in danger of unravelling even before it has begun.
Blues boss Conte has voiced his frustration at the lack of new signings, the squad looks wafer thin as they approach a new campaign on four fronts and Chelsea desperately need to change the momentum.
It does feel too negative, even Alvaro Morata - their biggest signing of the summer at £67m - was only a substitute and the way they allowed Arsenal to come back will be a major worry.
Arsenal played well, they showed a spirit lacking from Chelsea’s performance at times and Conte’s mood was as downbeat as Arsene Wenger’s optimism after winning the trophy with a penalty shoot-out.
Conte had every right to complain about Willian being booked for diving rather than being awarded what looked like a clear cut first half penalty.
And Conte had a point about the 81st minute red card for Pedro after the Chelsea winger raked his studs down Mohamed Elneny’s Achilles. It is, after all, a friendly. A yellow, quiet word and substitution should surely have sufficed.
But that was the cue for Arsenal to snatch an equaliser from the resulting free kick, Granit Xhaka’s wonderful delivery picking out substitute Sead Kolasinac who marked a highly impressive debut with a close range header.
In truth, it is all very well winning at Wembley on a gloriously sunny day - but it will not be enough to keep Arsenal fans happy.
They lifted the FA Cup in May, Olivier Giroud’s winning spot kick clinched the Community Shield, but their sights must be higher.
Even so, the traditional curtain raiser can set the tone and that will be the worry for Chelsea and the hope for Arsenal. Wenger’s men looked sharp from the start, Alex Iwobi and Danny Welbeck very lively while Alexandre Lacazette hit the post.
Arsenal were the better team first half despite losing Per Mertesacker after his clash of heads with Gary Cahill. But his replacement Kolasinac came on after 32 minutes and looked rock solid and ready made for the Premier League.
Chelsea started the second half well, probably on the back of a half time rollicking from Conte.
Willian’s corner resulted in a poor clearance from Xhaka, Cahill headed the ball back and Victor Moses stormed in to fire home. From red card villain in May to redemption in August.
Arsenal did not let heads drop and kept fighting.
Kolasinac’s equaliser took it to penalties. Now with the new ABBA style of shoot-outs, Gary Cahill went first and scored but from then on it went downhill fast with Thibaut Courtois inexplicably taking the second and blasting it over.
Morata also missed while Theo Walcott, Nacho Monreal, Alex Oxlade-Chamberlain and then finally Giroud were on target to start the Arsenal celebrations.
Giroud is fighting for his future after Lacazette’s arrival and he is not giving up without a fight.
Giroud got a huge reception from the Arsenal fans as did Alexis Sanchez who joined in the celebrations despite not yet being fit to play.
The mood is certainly more upbeat in the red half of London while it feels all too blue for the defending champions.