Tottenham let slip a two-goal lead before suffering shootout pain in Thomas Frank’s first match in charge to lose a thrilling Super Cup final against Paris Saint-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 shootout 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.
This fixture marked Romero’s first official match since being appointed Spurs captain, following Son Heung-min’s departure, and he lined-up in a back-three as Frank immediately stamped his authority.
Tottenham edged the opening stages before PSG attacker Khvicha Kvaratskhelia dragged wide to provide a reminder of his talent.
Chances remained limited until Richarlison let fly from 20 yards but PSG debutant Lucas Chevalier – preferred to Italy’s Gianluigi Donnarumma – tipped over.
Mohammed Kudus, on his first start since a summer switch from West Ham, almost tested Chevalier again only for Marquinhos to come across to make a crucial block.
A sliced Van de Ven clearance presented a chance for Ousmane Dembele moments later but he fired off target and then Tottenham grabbed their opening goal under new boss Frank.
It was from a set-piece as Guglielmo Vicario’s diagonal to the back post was headed into the penalty area by Romero and, even though Palhinha had a close-range effort pushed onto the crossbar, Van de Ven slid home to spark big celebrations.
A second nearly followed but Kudus’s stabbed effort hit the post to ensure it stayed 1-0 at half-time.
Three minutes into the second half and Frank watched Spurs grab a second.
Another set-piece did the trick as Porro picked out the unmarked Romero at the back post and his header into the ground slipped through the hands of Chevalier in a moment he would want to forget in the homeland of Donnarumma.
Kevin Danso sent another effort into the side-netting in the 52nd-minute before Luis Enrique went for broke.
Last-ditch defending by Romero thwarted one chance before Van de Ven slid in to deny the lively Desire Doue.
PSG had the ball in the net after 66 minutes but Bradley Barcola’s strike was disallowed for offside in a move which saw Danso produce a heroic block to prevent Fabian Ruiz from scoring after Vicario had saved from Doue.
Tottenham continued to be pinned back and, not long after Djed Spence blocked an effort by Dembele, PSG reduced the deficit.
Substitute Lee arrowed an effort into the bottom corner with five minutes left to set up a nervy finale.
Eventually the pressure told as Achraf Hakimi slipped in Dembele, who crossed for Ramos to head home the leveller in the fourth minute of stoppage-time.
Spurs were left crestfallen but gained two early advantages in the shootout when captain Romero called correctly to ensure spot-kicks were taken in front of their fans and when Vitinha sent his effort wide.
When Rodrigo Bentancur scored, Tottenham were 2-0 up but Van de Ven was denied by Chevalier and Tel fired off target to allow Nuno Mendes to tuck away the winning spot-kick.
