Tottenham threw away a two-goal lead to lose the UEFA Super Cup lead to Paris Saint-Germain.
Micky van de Ven and Cristian Romero scored either side of half-time had looked set to give Thomas Frank a dream start in his first competitive game as Spurs boss.
PSG appeared rusty until Luis Enrique changed both his gameplan and his selection with an hour gone.
The introduction of Fabian Ruiz made a particular impact as Spurs tired, and their backline was finally breached in the dying minutes as fellow substitute Kang-In Lee rifled in from the edge of the box.
Tottenham still seemed likely to hold on for a second trophy in less than three months with their advantage in tact until the 94th minute – when Goncalo Ramos’ stooping header sent the game to the lottery of penalties.
True to form, Spurs took the lead in the shoot-out after Vitinha missed PSG’s first kick, but once Van de Ven and Mathys Tel both failed to score from 12 yards, Nuno Mendes stepped up to cement their heartbreak as the French champions bounced back from that Chelsea loss by the barest of margins.
