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European champions Paris St-Germain produced a superb late recovery before winning a penalty shootout to clinch the UEFA Super Cup and deny Thomas Frank a first trophy as Tottenham boss.
Spurs led 2-0 after 84 minutes and were then seconds away from clinching an impressive victory before PSG substitute Goncalo Ramos headed in a 94th-minute equaliser.
That took the tie straight to penalties and PSG missed their opening effort as Vitinha fired wide, but Micky van de Ven, who had scored Tottenham's first goal earlier on, had his spot-kick saved by Lucas Chevalier.
Mathys Tel shot wide for Frank's side before Nuno Mendes held his nerve to convert the winning penalty for PSG.
It meant Tottenham missed out on winning a second European trophy in three months.
Frank was taking charge of Tottenham in a competitive match for the first time since he replaced Ange Postecoglou, who was sacked 16 days after guiding the club to a 1-0 victory over Manchester United in the Europa League final in May.
Van de Ven put Tottenham ahead in Udine, Italy, reacting first to slide in the rebound after Chevalier had tipped Joao Palhinha's effort on to the crossbar just before half-time.
Chevalier - expected to be PSG's regular goalkeeper this season after Gianluigi Donnarumma was surprisingly left out of their squad - was beaten again early in the second half when he got two hands to Cristian Romero's header following Pedro Porro's free-kick but could not keep the ball out of the net.
But PSG, who only returned to training a week ago after losing to Chelsea in the final of the Club World Cup in the United States in July, fought back in style.
Lee Kang-in started the recovery with an excellent strike from 20 yards, before Ramos dramatically took the tie to a shootout with PSG triumphing.
Analysis: Heartbreak for Spurs but plenty of encouraging signs for Frank
Before the match, PSG captain Marquinhos walked on to the pitch holding the Champions League trophy, while Romero, announced as Spurs' new captain earlier on Wednesday following the transfer of Son Heung-min to American side Los Angeles FC, held the Europa League trophy.
But by the end of the night in Italy, Marquinhos was lifting the Super Cup aloft as PSG won this competition for the first time in their history.
However, Spurs will be left wondering how they missed out on what would have been their fifth European trophy.
Postecoglou steered Tottenham to their first piece of silverware in 17 years, but that was not enough to keep him in a job as a miserable season domestically ended with them 17th in the Premier League, their lowest position since one season in the old Second Division in 1977-78.
Many Spurs fans felt Postecoglou deserved to keep his job, only for him to be replaced by Dane Frank after his near seven-year successful spell at Brentford.
But Tottenham supporters - some of whom are planning to hold a protest on Saturday before their Premier League opener against Burnley, angry at owner Daniel Levy and the club's perceived lack of activity in the summer transfer market - will have been pleased with the team's performance in Italy, despite the disappointing outcome.

Tottenham conceded 65 Premier League goals last season, the fifth worst defensive record, but with Frank utilising a back five when out of possession, Spurs denied PSG a shot on target for 65 minutes.
Indeed, Spurs looked in control, before PSG showed their spirit to gain their fifth victory over an English team in 2025 after beating Manchester City in the Champions League group phase, Liverpool in the last 16, Aston Villa in the quarter-finals and Arsenal in the semi-final.
One source of encouragement for Spurs fans will be the danger their team posed at set-pieces, with both of their goals coming shortly after free-kicks.
For the first goal, keeper Guglielmo Vicario, just inside the PSG half, angled a delivery to the back post, where Romero headed it back into the danger zone, Van de Ven caused problems and - after the ball had dropped for Palhinha - was well placed to convert the rebound.
Spurs' second also came from a set-piece, with Porro's free-kick finding the head of Romero, although Chevalier should have done better with the effort.
Nevertheless, the evening ultimately ended in disappointment for Tottenham who have only three days to recover before the start of the Premier League season.
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