London - Monaco ruined Tottenham's record-breaking night-out at Wembley as the French side earned a 2-1 win in their Champions League Group E opener on Wednesday.
Tottenham are back in the Champions League for the first time in five years and, with the capacity at their White Hart Lane stadium reduced due to redevelopment, they opted to play their European matches at Wembley this season.
Off the pitch, the move was a resounding success as a record home attendance for an English club of 85,011 packed into Wembley, surpassing the previous high of 84,467 set by Manchester City for an FA Cup tie against Stoke at Maine Road in 1934.
The iconic Wembley arch was lit up in Tottenham's blue and white, but that was the extent of the home comforts for Mauricio Pochettino's side as they paid the price for a sloppy first-half display.
Goals from Bernardo Silva and Thomas Lemar put Monaco in command and although Toby Alderweireld got one back, Tottenham were unable to turn their second-half dominance into an equaliser.
It is not the first time an English team has come unstuck after making Wembley their temporary home as rivals Arsenal also struggled there for two Champions League campaigns in 1998 and 1999.
It might have been different if Tottenham had taken an early chance when Harry Kane whipped over a teasing cross that Monaco defender Andrea Raggi made a hash of clearing.
Son Heung-Min pounced on the loose ball and drove his shot under goalkeeper Danijel Subasic, only for Raggi to scramble to his feet and redeem himself with a goal-line clearance.
Ligue 1 leaders Monaco have already beaten French champions Paris Saint Germain this season, as well as surviving two qualifying rounds to make the Champions League group stages.
And amid a raucous atmosphere, Leonardo Jardim's team stunned Wembley into silence in the 15th minute.
Tottenham winger Erik Lamela was guilty of an errant pass that deflected towards Silva 30 yards from goal and, with Pochettino's defence caught flat-footed, the Portugal midfielder was allowed to advance unchecked before lashing a fine finish past Hugo Lloris from the edge of the penalty area.
Tottenham have won only once at the redeveloped Wembley since it opened in 2007 and Monaco's goal must have brought back unpleasant memories for Pochettino's team, who lost the League Cup final against Chelsea on their last visit.
It certainly appeared they were rattled when Monaco punished more careless defending to double their lead in the 31st minute.
Djibril Sidibe was granted time and space to hoist a cross into the six-yard box and Jan Vertonghen's mistimed attempt to head clear deflected into the path of Monaco substitute Lemar, who crashed a powerful strike into the roof of the net from close range.
Desperately in need of a response before half-time as their supporters began to vent their frustrations, Tottenham finally found some momentum and were rewarded in the 45th minute when Belgium defender Alderweireld powered his header past Subasic from Lamela's corner.
Pochettino sent on Mousa Dembele for Son at half-time and the Premier League side almost had an instant equaliser as Dele Alli's dipping half-volley from 25 yards drew an agile tip-over from Subasic.
Tottenham thought they had been given a penalty when Monaco midfielder Fabinho was booked for tangling with Alli before a corner, but the offence couldn't be punished with a spot-kick because the ball wasn't in play.
Kane had been held in check for much of the evening and when the England star finally had a clear sight of goal from Vincent Janssen's pass, he wasted Tottenham's last chance with a hurried shot straight at Subasic.