Tottenham Hotspur took a two-goal lead in the Super Cup final, which was Thomas Frank's first under management, but eventually lost on penalties to Paris Saint-Germain after a tense encounter.
Set-piece goals from Micky van de Ven and Cristian Romero put Spurs on course for a possible trophy, just three months after Frank's previous boss, Ange Postecoglou, secured the Europa League title in May.
Champions League winners PSG, who only returned to training last week after playing in the Club World Cup in July, responded brightly as Lee Kang-in reduced the deficit with a goal five minutes from time.
Substitute Goncalo Ramos forced a penalty with a header in the fourth minute of added time to stun the north London side.
Tottenham looked more confident early in the shootout when Vitinha missed PSG's first attempt, but Van de Ven and Mathis Thel then failed to score and Luis Enrique's side won 4-3 on penalties despite Frank's impressive debut performance.
The match was Romero's first competitive match since being appointed Spurs captain following the departure of Son Heung-min. He came on as part of a back three and immediately showed his strength.
Tottenham dominated the early going until PSG striker Khvicha Kvaratskhelia stepped up to show his talent.
Chances remained limited until Richarlison fired home from 20 metres out, but PSG debutant Lucas Chevalier, who started in place of Italian Gianluigi Donnarumma, was unable to beat his opponent.
Mohamed Kudus, making his first start since joining from West Ham, almost tested Chevalier but Marquinhos made the decisive block.
A short time later, Van de Ven made a sharp clearance, giving Ousmane Dembele a chance, who shot wide of the goal, and then Tottenham, under new manager Frank, opened the scoring.
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