Tottenham's dreams of qualifying for the Champions League group stages hang in the balance after a first leg play-off defeat by Young Boys.
Senad Lulic slotted the home side ahead before Henri Bienvenu burst though and and expertly side-footed in.
Xavier Hochstrasser fired in a third for Young Boys after just 30 minutes.
Sebastien Bassong headed in for Spurs and Roman Pavlyuchenko lashed in a shot late on to give the visitors hope of overturning the deficit.
Spurs had not played in European football's top competition since reaching the semi-finals of the European Cup in 1960/1961.
The English side were dreaming of again mixing it among Europe's elite after getting what many perceived as a favourable draw against Young Boys.
But the Swiss side had other ideas as Spurs failed to deal with the plastic pitch and froze under the weight of expectation in an opening half which left boss Harry Redknapp to look on in horror.
Spurs were a shadow of the side that played with such verve in the goalless draw against Manchester City on Saturday and they had an early reprieve when Lulic managed to get a shot in from the edge of the box only to see it come back off the post.
The visitors failed to heed the warning sign and went behind when a Thierry Doubai strike ricocheted off Ammar Jemal, who appeared to be offside, and fell for Lulic to guide home an angled shot from eight yards.
Spurs did have a chance to level when Giovani dos Santos produced a surging run into the Young Boys area but his effort was blocked by keeper Marco Wolfli.
Dos Santos started as one of four changes made by Redknapp, who left Tom Huddlestone and Aaron Lennon on the bench for fear of the duo getting injured on the artificial surface.
Redknapp also went for an attacking 4-4-2 formation and, whether or not there was hint of complacency in his team and tactics, a stunned Spurs quickly found themselves further behind.
Pavlyuchenko gave the ball away and Doubai prodded the ball through to Bienvenu, who left defender Michael Dawson in his wake as he burst through on goal and expertly slotted in.
Tottenham's nightmare got worse when Young Boys playmaker Costanzo threaded a pass through the visitors' flat-footed defence and Hochstrasser powered in a shot.
A Jemal free-kick flew just over before Redknapp took action by taking off left-back Benoit Assou-Ekotto for central midfielder Huddlestone after 35 minutes.
The visitors eventually started to come to terms with the surface and occasion and pulled a goal back when Bassong headed in Gareth Bale's corner.
Pavlyuchenko had a promising chance to reduce the arrears even more, although he could not divert in a Bale cross with his outstretched leg at the far post.
The near miss served to provide Young Boys with the motivation to increase their efforts as they defended their lead with a discipline and drive as Spurs struggled for another breakthrough.
Indeed, Young Boys came the closer to adding to their lead when Bienvenu out jumped Bale to head over and Christian Schneuwly twice fired over in quick succession to the relief of the Spurs contingent.
Those misses proved crucial as Pavlyuchenko latched on to a Robbie Keane pass and angled a thunderous shot into the top corner late on to leave Spurs with the hope of completing their comeback in the return leg.