Brazilian full back Gilberto had a nightmare debut as his mistake allowed Jefferson Farfan to give PSV a first leg lead ahead of the return trip to Eindhoven next week.
The left back conceded possesion when he tried to run his way out of trouble 25 yards from goal.
Peruvian striker Farfan intercepted the ball and fired a sublime finish past Paul Robinson.
It was one of several errors made my debutant Gilberto, who was also booked before being replaced by Jamie O'Hara at half-time.
And PSV could have finished the tie as a contest spurning several chances as Spurs went for broke in the second half.
Spurs had plenty of possession but struggled to create any clear-cut opportunities.
Juande Ramos had fielded a strong line-up including captain Ledley King and Carling Cup matchwinner Jonathon Woodgate returning to central defence.
But Spurs fell to only their third White Hart Lane defeat in European Competition, leaving Ramos' side needing an inspired performance in Eindhoven next week.
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