A night of Champions League history for Cristiano Ronaldo ended in a stunning twist as Young Boys staged a memorable fightback to beat 10-man Manchester United 2-1 in Group F.
United appeared set for a routine victory in Berne when Ronaldo, who had scored twice on his second debut for the club against Newcastle United on Saturday, put them ahead in the 13th minute.
But Aaron Wan-Bissaka's red card late in the first half gave Young Boys hope, which was realised when Nicolas Moumi Ngamaleu levelled matters with a 66th-minute strike.
Ole Gunnar Solskjaer's men looked set to emerge with a creditable point having defended for close to an hour a man down, yet there was a remarkable late twist as Jesse Lingard misjudged a backpass and Jordan Siebatcheu slotted past David de Gea to secure a famous result for the Swiss side.
Ronaldo squeaked the opener through the legs of David von Ballmoos, who could not prevent the ball crossing the line after the Portugal star latched on unmarked to a superb delivery with the outside of the boot from compatriot Bruno Fernandes.
Von Ballmoos fared better second time around to deny Ronaldo at his near post at the end of a quick counter, with David de Gea forced into a diving save from Christian Fassnacht's long-range effort moments earlier.
But the complexion of the game was altered in the 35th minute when referee Francois Letexier had no hesitation in showing Wan-Bissaka a straight red card for going over the top of the ball and catching Christopher Martins Pereira on the ankle.
Jadon Sancho was replaced by Diogo Dalot to fill the void left in United's defence, which coped well until under persistent pressure until Ngamaleu poked home at the near post from Silvan Hefti's low right-wing delivery.
United appeared poised to escape with a point but Lingard's loss of composure presented Siebatcheu with a simple finish to send the Wankdorf Stadium into delirium with the final kick.
What does it mean?
In contrast to their peerless form on the road in the Premier League, away shortcomings were a significant factor in United's undoing in last season's group stage as they lost at Istanbul Basaksehir and RB Leipzig.
And another disappointing performance away from Old Trafford cost them here, with United losing after leading at half-time in the Champions League for the first time since March 30 2010 against Bayern Munich, a run of 22 games coming to an end.
Young Boys get just reward
Though United had more possession in the first half, Young Boys had more opportunities, tallying eight shots to the visitors' two.
They were dominant in the second half with the extra man, penning United in their own half and attempting a further 11 shots, the last of which saw their energy rewarded with a deserved victory.
Ronaldo records overshadowed
Ronaldo made his 177th Champions League appearance, tying the record set by former Real Madrid team-mate Iker Casillas, and marked it with a goal that saw him move level with Lionel Messi by scoring against a record 36th different club in the competition.
The gap of 12 years and 132 days between Champions League goals for the same club is the biggest in the competition's history, breaking Javier Zanetti's record of 11 years and 315 days for Inter (1998-2010). None of that will matter to him now, though, following a damaging defeat.
Key Opta facts
- Siebatcheu became the first player to score a 90th-minute winning goal against Manchester United in the Champions League since March 2010, when Ivica Olic did so for Bayern Munich in that season's quarter-final.
- Timed at 94 minutes and 22 seconds, Siebatcheu's strike was the latest winning goal in a Champions League match since Lucas Moura’s goal for Tottenham against Ajax in May 2019 (95:01).
- United managed just two shots in this match, the fewest Opta have on record in any of their 138 Champions League matches since 2003-04. Their second and final shot of the match came in the 25th minute from Ronaldo.
- United have lost their first match in a Champions League campaign for only the second time, also doing so in 2015-16 under Louis van Gaal, a 2-1 defeat to PSV.
- Wan-Bissaka became the first United player to receive a straight red card in the Champions League since Nani in March 2013 against Real Madrid, and the first Englishman to receive a straight red since John Terry for Chelsea against Barcelona in April 2012.
United visit West Ham on Sunday in the Premier League, when Young Boys will experience a very different test, a Swiss Cup clash with fifth-tier side Iliria.