Tottenham yielded a late two-goal lead before suffering shoot-out pain in Thomas Frank's first match in charge to lose a thrilling Super Cup final against Paris St Germain.
Set-piece goals by Micky van de Ven and Cristian Romero had Spurs halfway towards another trophy - only three months on from Frank's predecessor Ange Postecoglou clinching Europa League success in May.
Champions League winners PSG, who only returned to pre-season last week following their Club World Cup exploits in July, produced a stirring response with Kang-In Lee pulling one back with five minutes left.
Substitute Goncalo Ramos forced spot-kicks when he headed home in the fourth-minute of stoppage-time to stun the north London club.
It was initially advantage Tottenham in the shoot-out when Vitinha missed PSG's first kick but it was followed by Van de Ven and Mathys Tel failing to score their penalties as Luis Enrique's men triumphed 4-3 on spot-kicks despite a fine display on Frank's competitive debut.
