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Spurs got off to a nightmare start, going three down within the first half hour as the Bernese side took full advantage of their artificial pitch.
The Premier League side later pulled two back through Sebastien Bassong and Roman Pavyluchenko and stifled the Young Boys' ardour, easing the task for return leg on grass at White Hart Lane and leaving the Swiss underdogs to rue missed opportunities.
Two minutes after the kick-off, Young Boys' midfielder Senad Lulic set the tone, with a shot that bounced off the Londoners' post with Heurelho Gomes beaten.
The Bosnian took advantage of a kind bounce off another Bernese player's back moments later to slot the loose ball past Gomes.
But it swiftly became clear that the Swiss did not need a stroke of luck to get the better of Spurs's unsettled defence.
Young Boys Henri Bienvenu made it 2-0 in the 13th minute, after the Londoners lost the ball in midfield.
A pass from the Swiss half split Tottenham's defence through the middle, allowing the Cameroon international to outpace Michael Dawson and wrong-foot Gomes with a deft finish.
The Bernese seized a third a quarter of an hour later as Xavier Hochstrasser sneaked behind the Spurs left back to pick up a superbly weighted pass by Swiss international hope Moreno Costanzo.
Tottenham nonetheless seized a vital away goal from a corner two minutes before half time.
Bassong outleapt the Swiss defence and placed a sizzling header above Woelffli's head.
Playing with Pavlyuchenko instead of the lanky Peter Crouch upfront, Tottenham ultimately capitalised on the Russian's previous experience of the speedy artificial pitch in the second half.
Harry Redknapp brought on Niko Kranjcar for his largely ineffective fellow Croat Luka Modric in midfield, allowing Spurs to dampen the Young Boys growing confidence, while Robbie Keane displaced Jermain Defoe.
Pavyluchenko was both at the origin and finish of the flowing move with Keane that produced the Premier League side's second goal in the 82nd minute.
But the hungrier looking Swiss almost volleyed in two more on the break, adding to the warning signals for the return leg in London.
"It might be easier for us to go there and attack rather than sit back and defend," said Hochstrasser.
"The first half hour wasn't good enough, but we stuck together and sorted it out at half-time," said Spurs centre-back Dawson.
Both Tottenham and Young Boys are aiming for a historic first step into the Champions' League.
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