Gilberto suffered a nightmare Tottenham debut as PSV Eindhoven earned a slender 1-0 UEFA Cup last-16 advantage to take to Holland next week.
Spurs coach Juande Ramos billed Thursday night's White Hart Lane clash as the barometer of whether his side could win the competition - but it was the Dutch champions that looked more likely to be at Eastlands in May.
Although it was a deflating evening for Ramos' players, none were as disappointing as Gilberto; the Brazil full-back was booked, was at fault for Jefferson Farfan's 34th-minute winner and was taken off at half-time.
For the goal, Aaron Lennon's poor free-kick was cleared and Farfan broke forward.
Lennon did get back to intercept but when the ball fell to Gilberto, the full-back took a touch too many and Farfan dispossessed him before finishing powerfully beyond Paul Robinson.